


Now That's Comedy

by CaptainMercy42



Category: Supernatural
Genre: AU, Adopted Castiel, Alternate Universe, Casual Sex, Comedian Castiel, Comedian Gabriel, Comedy, Destiel - Freeform, F/M, M/M, Sheriff Jody Mills - Freeform, Slow Burn, Stand Up Comedy, comedian dean, comedian sam, sheriff donna hanscum, stand up comedians, they're all comedians, uber religious upbring castiel
Language: English
Status: In-Progress
Published: 2015-11-28
Updated: 2016-07-03
Packaged: 2018-05-03 18:27:11
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 22,272
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5302124
Author URL: https://archiveofourown.org/users/CaptainMercy42/pseuds/CaptainMercy42
Summary: <blockquote class="userstuff">
              <p>Comedy. It's what Winchester's did. Winchester's, and about a million other dumb fucks with an iPhone and 140 character witticisms about their first world problems. It was not supposed to bug him when no-talent "wordsmiths" got highlighted in a bit on Ellen or Bob and Tom. But it did. </p><p>His dad, well he was great at it. It was dark comedy. It came from a dark place; the loss of a wife and the life of a morally bankrupt single dad, almost innocent in how thoroughly unprepared he was for fatherhood.  Substance abuse in itself provided jokes for days. The material actually outlasted his dear old dad. This surprised no one. What was surprising was Sam's decision to ditch college and do his own act, despite his lingering bitterness. </p><p>The first night Dean saw Sam perform was also the first night Dean saw Castiel perform.<br/>**I apologize for having this show up as complete before. Oops. **</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> To be 100% open and honest, I've been sitting on this story in my head for a long while, and I'm just down and out enough at this moment to be fishing for some positive comments - hence I am now posting chapter 1 without having the rest of it fully written. Updates will not be on a schedule, and I'm known to be slow (but always finished, eventually). I do really, really want to finish this.
> 
> ALSO, for a while I wouldn't read anything with my OTP sleeping with other folks - so I feel you if you're not into that. However, the characters in this AU are all really cavalier about sex, and I'm not really planning any jealousy. It's a jealousy free fic, I think. So there's that.

Dean and Sam lived in the octagon house on Spruce Street. Surprisingly enough, that was a pretty successful pick-up line that they were both slightly ashamed to say they’d used repeatedly.  Apparently, after midnight, certain drunk girls were intrigued when they found out a hot guy’s bedroom may have more than four walls.  Other girls knew it was a notorious party spot. To them, saying you lived in the octagon house was essentially touting your good reputation for offering up a safe one night stand with absolutely no chance at ever getting called back for a second romp.  It was the phrase of doom for any girl who had monogamous designs on Sam, who had been known to get all squishy and dateable a time or two, but never with his walk-of-shame victims.

For Dean, it was freedom. Freedom to finally stop performing and get down to business. He didn’t know how girls did it, day in and day out with their clothes and their makeup and their bubbly personalities. He had enough trouble smiling and grimacing on cue during a 15 minute open mic.  By the time he'd sat through Sam and whoever else was on the hook that night, he was thoroughly fatigued from whispering his criticisms of the crowd and the performer alike, to no one in particular.  He was then expected to bullshit his way into bed with the cutest girl who casually complimented his set? Fuck that noise. "Did you know I live in the octagon house?" was about all he could muster at that point. It hadn’t failed him yet, (but who are we kidding, his perfect fucking face helped his game about three times as much as it hurt his act).

Comedy. It's what Winchesters did. Winchesters, and about a million other dumb fucks with an iPhone and 140 character witticisms about their first world problems. It was not supposed to bug Dean when no-talent "wordsmiths" got highlighted in a bit on Ellen or Bob and Tom. But it did.

His dad John, well he was great at it. It was dark comedy. It came from a dark place; the loss of a wife and the life of a morally bankrupt single dad, almost innocent in how thoroughly unprepared he was for fatherhood.  Substance abuse in itself provided jokes for days. The material actually outlasted his dear old dad. This surprised no one. What was surprising was Sam's decision to ditch college and do his own act, despite his lingering bitterness.

At first, Dean was sure that that was all he was gonna hear in Sam's jokes - slams against his dad and his childhood and how ruined Sam was for "normal" relationships thanks to all the bullshit. The best comedy was supposed to come out of the worst experiences. But just because Sam quit school didn't mean he'd forgotten how to be a genius. John Winchester was a jerk, but he was a full fledged performer. An entertainer. An artist. And Sam was his son, apparently also not content to let the coddled one-liner tweeters of the upcoming generation completely obliterate the art of stand-up comedy.  Sam knew intrinsically what mechanisms were at work in a good routine, and Dean never felt more proud of his little brother than he did when he watched his first open mic.

"First off, I need to apologize." Sam started, with a mischievous sad puppy face. "I'm incredibly tall."  The kinder, looser audience members giggled. "I had no idea, until someone told me earlier, backstage.”  He gave them a look of sheer naivety, then let it crack into a knowing smirk.  “I love being told that. It saves me from giving two shits about how I look.  Who cares, right?  I’m a walking Rorschach inkblot that provokes ‘tall’ in 90% of the population." He shrugged. "I can handle that." He fiddled with the mic stand in an expert way that might have been embedded in his genetic code. "Because I know there is going to come a time when people will meet me and NOT tell me I'm tall, and that will mean that I have a new defining trait. Something that you are not allowed to just blurt out at people, like 'In an earthquake, I would be afraid your forehead might topple over and crush me!'" He put on a funny, high pitched voice for his quoted bits. "I could always just assume that people's first thought is 'wow, he's so handsome!' Because, unfortunately that's just not something we, as men, feel comfortable telling each other- which is just too bad." Sam smiled his most winning smile.

"You're hot!" A drunk girl hollered from her seat at the bar.  The audience tittered.

“You see?  Thank you.”  Sam gestured towards the voice.  “Your voice is very feminine.”

Dean wondered if Sam would lose his footing after bantering with the hecklers- if the whole set was just a randomized list of pleasant observations.  He didn’t wonder long, as Sam began to quickly weave an engaging story of puns and quips with only occasional pauses to allow the callbacks to his previous lines to pierce through the drunkenness and hit home.  Of course. Only Sam would start off a 10 minute slot at an open mic as if he were carefully easing himself into an hour long HBO special.  Dean was clapping the loudest, with a tear in his eye when Sam finally waved and said, “well, that’s my time,” hopping off the 8” stage, and still towering over the audience, perched at their high tables.

“How was it?” He asked Dean, slicking his hair back with two hands for no reason other than nervous movement and the dispersion of sweat.

“It was awesome.  Seriously.  You got the gentle giant thing going, then you hit ‘em with the sarcastic stuff later.  It was great.”  Dean patted his brother on the shoulder.  “You wanna get out of here?”

“Nah, let’s stick around.  I wanna drink.  I’m jittery.”  Sam was off to the bar with a nod.

The first night Dean saw Sam perform was also the first night Dean saw Castiel perform.  He was the next guy called up to the stage by the wild and zany open mic host.  Sam had brought Dean a beer and Dean was content to have zoned out for a minute, until a very serious, and gravely voice came through the PA.

"Thank you for that colorful introduction, Gabriel. Hello. I am Castiel.  But first, let’s hear it for Sam.  He was ...handsome."  The crowd whooped for Sam, and appreciated Castiel’s callback.  

Dean smirked, and took a moment to stare down this Castiel.  He was tall, with dark hair and a five o’clock shadow that highlighted his angular jaw.  He was dressed in a white shirt and black slacks that could have been purchased at Wal-Mart, all partly obscured by a tan trench coat that might have cost a lot when it was new, twenty years ago.  

“You will have to excuse me if my people skills seem a little rusty.”  Castiel continued, examining each member of the front row with unbridled intensity.  “I was adopted by very strict religious parents, and home-schooled all my life so that I could become a valiant soldier in the Lord’s army.”  People literally groaned out loud.  “There were 12 of us.  My mother originally only wanted three children, but someone was kind enough to tip her off to the desertion statistics for this particular war with the devil. ”

“In addition to beating us with a belt when we misbehaved, and forcing us to memorize long passages of scripture, my mother could also be cruel."  Dean didn't know if uncomfortable laughter was desirable, but  it was becoming bountiful.  

"She was strongly against vanity, but she discovered the intrinsic value of orthodontry as a form of punishment." He licked his perfect teeth, seemingly lost in thought.  “She nearly rejoiced herself off the porch and into the rose bushes when she heard my eye teeth were impacted.”

Dean cringed.  Everyone probably cringed.  Teeth are a sensitive subject, and the thought of a parent (albeit adoptive) delighting in the pain they cause was rather grotesque.  Castiel did manage to lighten it up a little, with anecdotes about the absurdity of the concept of heaven.  Dean was smiling, not exactly laughing out loud, but appreciating.

“If you are looking to turn a child off to an entire religion in one fell swoop, I would suggest informing them that the family dog does not have a soul, and will therefore not be admitted into heaven.  I have it on good authority that that child will never again worry about gaining admittance into heaven.”  Castiel nodded and stared, as if he were relaying the text of the US census.

"I may return to religion in fifty years or so.  From what I have read, by that time science will be advanced enough that we can collect a few weeks of communion bread and wine and engineer a new Christ. Do not get too excited." He gave a particularly tall girl in the middle if the audience a stern glare. "It might be awkward during the beginning phases when they haven't quite worked the kinks out. They may have Christs that only last hours, or maybe days at a time. There might be a Dolly the Christ. I suppose they could try to grow his organs in a genetically modified pig. I'm sure the Jews would find that offensive, but what better way to exercise man's dominion over the animals?"  

The audience all suddenly became perplexed. Dean could feel their brains at war with their smiles, holding back confused laughter for fear it wasn't entirely correct to find his bizarre statements funny. Castiel smiled for the first time as he also observed their confusion. His eyes crinkled around the edges and his teeth were perfectly white.

"Ah. I have never been able to figure out an acceptable end for that joke. If anyone can, please let me know after the show.  Go out with a crash, right?  Isn’t that what they say? That is my time. Thank you. "

A smattering of applause, and a few good-hearted cheers followed Castiel off the stage.  He weaved around the crowd to the bar, then turned and approached the little hallway to the bathrooms where Dean happened to be leaning, his arms crossed over his chest.

“It’s ‘with a bang’.”  Dean half-shouted at Castiel as he breezed by, trench coat billowing behind him, as yet undecided about appearing heroic, or possibly like a crazed gunman.  Castiel stopped abruptly and turned to face Dean.

“Excuse me?”  

“You’re supposed to ‘go out with a bang’.”  Dean’s voice rose at the end of the statement, suddenly unsure as to whether Castiel had purposely butchered the saying.

“Oh.  Alright.  Do you know what bang it is referring to?”  Cas furrowed his brow.  Dean scratched his chin, absently.

“Uh.  I’m not sure.  It’s just how the saying goes.”  He squared his shoulders.  “I have an end for your Christ-in-a-lab joke too.”  

Castiel tilted his head forward, turning his face away so that his ear could be closer to Dean’s mouth.  Dean took it as a sign to continue.

“Well I haven’t gotten your cadence down, but you could do a play on those accident signs in factories-”  Cas’s eyes squinted at nothing as he still gazed at the bar.  “- you know, something like ‘this lab has gone 25 days without killing the savior of mankind’.”  Castiel straightened up and peered at Dean with clear, blue eyes.

“What do the signs usually say?”

“Uh, they usually say ‘this factory has gone blank days without an accident’.”

“And then a foreperson fills in the correct number?”

“Well yeah.”

Castiel glanced at the floor for a moment as he scratched the back of his neck.  Dean just stared, because he was knee-deep in one of the most awkward conversations of his lifetime, so he figured he might as well make the most of it.

“Where do you live?” Cas asked, finally.

“The octagon house.”

Cas’s face brightened, and he began to look mischievous.

“Now that I have heard of.  You’re Dean Winchester.”  He grinned as if he thought he were incredibly lucky.

“That’s me.”

“Is there any chance you’re looking for a roommate?”  The curiosity burning in Cas’s eyes could only mean that he was very interested in living in the octagon house.  Or with Dean.  Or with Dean and Sam.  Well that was strange.

If Dean had simply taken Castiel’s phone number and let his conscious mind be in charge of his decision making process then Castiel never would have received a callback from the famed Dean Winchester.  But as it happened, Dean and Sam had a full one and a half empty bedrooms (there was heated debate still raging about whether the ½ bedroom was really a very large, triangular closet).  They were making ends meet with the bits of this and that, plus their comedy, but winter was on its way and winter was never kind when you lived in a house that was more than 75 years old.

“I’d be willing to pay my share of the rent, as well as the full cost of heating.  I’m fiscally well-established, but I’m looking to make connections in the business of comedy.”  

 _Alright, he just read my mind._  Dean thought, as he stood there gaping.   _That’s not creepy, right?  If anything, it’s useful._

“Forgive me if this is forward, but it seems that you and your brother could be very useful to know.”

Fortunately, Sam saved Dean from visibly short-circuiting right there in the Laugh Shack hallway.  

“Hey, Dean, you’ve met Castiel!  Hello, Castiel.  That was a good set!”  Sam smiled, and the hallway to the bathrooms looked a little less dank.

“Thank you, Sam.  I enjoyed yours as well. Your brother was just helping me with the end of mine.  He is very astute.”

“Really?”  Sam made a show of looking impressed.  “Dean never helps anyone.  He must have really liked your stuff.”  Sam gave Castiel a good-natured clap on the shoulder, and Castiel grinned in response.  Dean felt that he now needed to squint in the sunshiny light of the hallway.

“That’s so far from the truth, it’s not even funny.  I help everyone.  If half the people I gave advice to bothered to take it, they wouldn’t still be hosting open-mics in Kansas.”

Dean raised his voice as the evening’s host came flitting by.  The man was older than Dean by at least ten years.  He was in a purple crushed-velvet blazer and black slacks that had their own sparkly sheen, and for some reason he was wearing a very undersized top hat perched askew on the front of his head, attached with a chinstrap.

“Sucking less cock and writing more jokes is advice my mother could have given me, Dean-o!  Now I just plug my ears and go ‘la la la la la are you famous yet?  Call me when you’re famous’.”

Dean just shook his head, with Sam mirroring the motion.  Gabriel spun away to harass a cocktail waitress while Castiel’s expression became pensive.

“I have been known to sleep with both genders, rather indiscriminately.  Would that be a problem?”

Sam’s eyebrows jumped to his hairline for a moment, before he had a mental ‘aha’ moment and collected himself.

“So you asked Dean about renting a room?”  

Castiel nodded.

Dean spent a fraction of a second being irrationally angry that Castiel did not simply decide after a 20 word conversation with Dean that he absolutely needed to live with Dean.  Instead, Castiel had established some kind of previous rapport with Sam, and they had presumably discussed the pros and cons of the idea, before even considering bringing the matter to Dean.  But because these thoughts occurred in only a fraction of a second, they were nearly subconscious, and Dean was simply left with the feeling one gets when one discovers an attractive individual was NOT just winking at them.

“Well look, Cas.  I’m not sure if we’re looking for a roommate, but I can speak for my brother when it comes to your sexual proclivities, and any orientation is totally fine.”  Sam patted Castiel on the shoulder again, more gently this time.  Dean returned from his trip to boohoo-ville, and decided that Sam needed to be put back in his place, after running around offering up rooms in their house without consulting him.  Two could play at this game.

“Yeah that’s not a problem.  We are definitely looking for a roommate, and as far as I’m concerned, you can move in any time.  What is today?  The 20th?”  He pointed at Sam and raised his eyebrows.  Sam nodded slowly.  “Great.  Yeah you can be in by next month if that works for you.”

“This is excellent news.”  Castiel smiled gratefully, and Dean’s heart melted a little, as if he didn’t just welcome a rich stranger into his home so that he’d have an excuse to keep the house at 70 degrees fahrenheit all winter long.

“Wow.  That’s awesome.”  Dean strained his ears in an effort to figure out if Sam was being entirely genuine.  “Welcome to the octagon house, man.”  Castiel beamed, and ducked his head.

“I’ll get us a round to celebrate.  But first, I’m going to use the little boys room, as I originally intended.”

Castiel breezed away towards the smellier end of the hall, and Sam cocked his head at Dean.

“You’re okay with him moving in with us, just like that?”

“Why not?  I assume you vetted him before telling him to ask me about the empty rooms in our home.”  Dean glared.

“He seems cool.  I mean I didn’t get references, but I told him you’d have to think about it.  You didn’t have to give him an answer right then.”

Dean dug a piece of pretzel out of top molar, with his tongue, and scowled a little, turning away from Sam and pushing on his rolled-up sleeves.

“Yeah, well.  What’s done is done.   If he sucks, the chances are he’ll get sick of us before we get sick of him.”

“Yeah.  And if it doesn’t look like he wants to leave, we can let Garth take the other bedroom.”  Sam stared at the stage as he said this, where a very tall but gangly man-boy was pulling a sock puppet onto his hand the way a doctor slides into a rubber glove.

“Who wants to hear Mr. Fizzles tell some dirty jokes?”  Garth asked with an infectious grin.  

“You mean the three walled closet that you have to go through the third bedroom to walk into?”  Dean smirked as he watched Garth suffer through the world's cheapest ventriloquist act.

“It also has a door leading to the bathroom!”  Sam insisted.

“Sammy.  Seriously.  No one wants to access their bedroom through a communal bathroom!”

“And no one puts a door to the bathroom in the back of a closet!”  Sam punctuated his point with a flap of his hand.

“There’s only one wall that you could even attempt put a bed against, and either way it’s going to block a door.  Forget a dresser."

“There’s a window! What closet has a window?”

“It’s stained fucking glass!”

They quickly decelerated after reaching their usual stalemate, just as two cold beers were pressed into their hands, and they noticed Castiel standing in front of them with his own brew.  He was glancing back and forth between them with a curious grin.  Dean sighed, shook his head, then toasted in gesture only.  Sam and Castiel followed suit, and they all three drank quietly, contemplating what exactly had happened, and how it was going to change their lives forever.


	2. Three's too much for a cupola

**Summary for the Chapter:**

> Cas fits right in, and comedy ensues.

“I have what's known as a ‘tiger mom’.”  The young man on stage was lean, of an average height and Asian descent.  “My childhood was hardcore: cello lessons, AP everything, going to be the first Asian American president.”  He punctuated his bullet points by making broad circles with his free hand.  “I hated it.  I wanted to rebel.  I wanted the other kids to see me as a real person and not just some Chinese math robot. I was more than just a stereotype, damnit!” He eyed the audience imploringly.  “ I begged and pleaded for her to please let me play a sport or get a skateboard or do anything to express my youthful, all-American personality.  So she signed me up for karate.”  He held the mic in a sort of prayer position with both hands as he let the punchline slide out.  “What? Elvis Presley was only happy when he practiced karate. What is more American than Elvis?” Kevin did a high, accented voice that had to be an impression of his mother. Sam and Dean smirked, having heard Kevin’s bit about his mom before.  Castiel looked on with curious intensity, and a small smile that hinted more at admiration than mirth.

“I’d like to say that going into comedy was the ultimate way to stick it to my mom, but it wasn’t.  She just shows up at my shows and tiger-mom’s me some more.”  Kevin shakes his head, no longer making eye contact with the crowd. 

“That’s my comedy genius!  My Chinese Jerry Seinfeld!”  A shrill voice rang out from the back of the room.  Castiel was startled, and turned to find the source.  Dean just chuckled and pointed to a table in the back where a petite Asian lady was sitting with her legs crossed, flipping through a fashion magazine.  The audience was still giggling at her outburst.

“Don’t encourage her, please!”  Kevin beseeched them.  “I mean, she’s pretty much harmless, but if you’re a middle-aged white guy in a suit she’ll start showing you my old report cards, on the off chance that you’re a TV talent scout… who’s lost… in Kansas.”  He looked at the ground again as people laughed. 

“I am enjoying this fellow.”  Castiel leaned towards Dean and politely spoke in his usual growl.  “Is that genuinely his mother?” 

“You betcha.”  Dean smiled.  “Mrs. Tran hasn’t missed a show yet.”

“That is admirable.” Cas looked very moved.

“Yeah.  Though it’s gotta be a little weird.  Doing stand-up comedy.  At a shitty bar.  In front of your mom.  I guess I wouldn’t know.” Dean coughed a little when he heard where he had taken the conversation. Castiel arrived in the same place with his usual stoic wonderment. 

“Hm.  I was told that my biological mother is deceased.  But I cannot fathom what it would be like to perform in front of my adoptive mother.” He shuddered.  “It sounds like something that would be prescribed by a therapist to help me achieve closure.”

Dean pulled a face at that comment, then toasted Cas’s beer just as Kevin finished his segment.  They clapped and cheered as he came off the stage, and Cas remained watching the front as if he had never before seen Gabriel kill 10 minutes trying to blow a fireball using 151 to the tune of Kelly Clarkson’s  _ Since you been gone. _

Dean took a couple of moments to examine Cas, in the erratic bursts of firelight.  They had been roommates for one week, and so far everything was very new and very… fine.  Dean had been concerned that having a virtual stranger in the house would throw him off.  He was anticipating getting that creepy-crawly feeling up his spine anytime he wound up with Cas standing behind him, perhaps trying to dig into the silverware drawer while Dean was cooking, or just staring at Dean’s choice of TV from the kitchen doorway.  He was worried that he wouldn’t be able to riff with Sam if they suddenly had an audience.

Dean’s worries were unfounded. He and Sam turned their riffing up to eleven now that they had Cas around to...well not exactly react, but he was always watching. Always. It wasn't an act. That was Cas. He was the kind of weirdo that could get completely high and then bake brownies from memory, while also roasting a chicken, at 11:30 PM, all while quoting random passages of scripture. In fact, he had done just that the night before when Pam had dropped off a bag of bud to welcome him to the neighborhood.  

Pam lived upstairs. On paper she was a psychic, but that was simply an excellent way to declare her drug-dealing income on her taxes (which she paid because “God bless fucking America, okay?”) . Otherwise she liked to run under the radar.  The Winchesters were good for her business, which is why she allowed them to create and nurture the Octagon House reputation. It was a fantastic excuse to have twenty-something year old kids on her doorstep, day or night. 

Castiel had listened to this explanation of their upstairs neighbor with intently, as he rubbed sage and butter into the skin of the small roaster he was suddenly craving.

“Is she single?” He questioned.

“For the most part. And you're just her type.” Dean smiled. “If she invites you up to see the cupola, you're in like sin.”

“What if I legitimately want to see the cupola?” Cas squinted. 

“Oh, you'll see the cupola, alright. And more.” Dean smirked. 

“She's kind if an exhibitionist.” Sam explained. “From what Dean actually remembers.” Sam smirked down his nose at his brother. 

“So you haven't both had liaisons with Pam?” Cas asked as he tented foil over the roasting pan. Sam laughed at the word “liaison”. Dean scowled a little. 

“Okay, so we're down with whatever, but for the record, Sam and me try not to ...overlap.”

Sam shuddered, and took a long sip of beer, swallowing hard and taking a breath before explaining. 

“Yeah. Something about when you find out her goal is to do both brothers… It's kind of creepy.” 

“Hell, Pam was trying for both of us at the same time. Eyuh. Just no.”

“I highly doubt the cupola could fit you both, simultaneously.” Cas observed, gravely. “But then again, it is easier for a threesome to fit through the eye of Pam’s...cupola than for a rich man to enter the kingdom of Heaven.” 

“Hey now, that’s blasphemy.” Sam faked shock.

“Blasphemy.  Comedy.  It’s a thin line, right Cas?  Fuck the rich.” Dean’s focus was getting hazy. Sam groaned. 

“Here, here.  Those who trust their riches will fall, but the righteous will thrive like a green leaf.”  Cas proceeded to take deep hit of his weclome joint.  Dean sauntered around the table and made a “gimme” motion with his hand.

“C’mon.  Blessed is the dude who passes the green leaf.”  Cas complied, and Dean took his turn.

“Is that why surfers call it  _ righteous bud _ ?”  Sam asked, doing his best exaggerated surfer dude voice. Cas considered the joke, and let a smile slide into his face before outright laughing. Maybe it was the weed, but he laughed and laughed, his deep, chesty rumble coaxing Sam and Dean into their own fits of manly giggles. 

“So.” Cas tried to rein in his mirth. “I am not your sibling. Will it be disagreeable if we… overlap? I would not want to make our living situation uncomfortable.”

Dean put his finger in his chin.  He had a tendency to over gesture when he was stoned. He pictured Cas putting the moves on -what was her name?  She was blonde and a waitress.  Yeah he was coming up empty.  He pictured Cas playing host to no-name the blonde, with himself running into her on his way to the bathroom or something, and then watching her slink back into Cas’s room.  It didn’t stir up any emotions.  If anything, he had to stop himself from imagining what might go on inside the room, without him.  Therein was the crux of the no-sharing-with-Sam issue.  It invited certain images into the mind that could never be unthought. 

“Ahem.”  Cas spoke the word, prompting Dean and Sam out of their trances.  He took a long lick of brownie batter off the scraping spatula, then offered the implement to Dean.  Dean took the spatula on autopilot, and shoved it in his mouth, moaning a little at the taste of homemade brownie batter, and the fleeting thought of what kinds of filthy things Cas could have done to Blondie the waitress with that dextrous looking tongue of his.

“You know what?”  Sam answered, not even cognizant of the spatula induced exchange of saliva betwixt his roommate and his brother.  He was hunched over with his elbow on the counter, pillowing his head with his forearm and cutting off some of his visibility.  “I think we’re all good on overlap.  That rule is just a thing for me and Dean.  Right, man?”  He raised his head to confirm with Dean.

“Yeah, I’m good.  Open season for Cas. Have fun with my sloppy seconds.”  Dean winked lazily, and whipped the thoroughly cleaned spatula at the sink.  Cas swallowed audibly, and stared unabashedly as Dean tried to locate errant chocolate in the corner of his mouth, with his tongue.

“Likewise.” Cas grated out, then he narrowed his eyes at Dean as if he were steeling himself to accept some some sort of unspoken challenge.  Dean’s mind applauded him for not dwelling on the fact that the last person who’d looked at him like that… well he’d got laid.

Dean was suddenly brought out of his introspective review of the previous night by a smattering of applause for the next performer.  It was a woman that Dean had never seen before, and to be honest, all this new comedy blood showing up in the middle of bumfuck Kansas was a little perplexing.  

“Hi, I’m Meg.”  The woman purred.  She was short, wearing black pants and a fit and feminine black leather jacket over a black top.  She smirked at the crowd with a certain look that Dean couldn’t quite put his finger on, but it made him uncomfortable.   He noticed Sam shifting his weight, folding his arms over his chest beside him, so maybe he wasn’t the only one affected.

“Mm. It’s like she knows I used to pleasure myself to the Chick tract about David and Bathsheba.”   Cas was suddenly close enough for Dean to feel light puffs of breath against his earlobe.  He shivered, but held back his initial reaction.

“I know, right?  She looks like the cat who just found women's underwear in my sock drawer.”  They were both entranced.

“So I’m gonna come right out and say it -”  Meg continued, taking a few sauntering steps around the stage, like she owned the place “- I’m addicted to sex, manipulation, guilt and money. What can I say, I’m a Catholic girl, through and through.”

“Oooh.”  Dean elbowed Cas, lightly.  “You gonna invite her to the Octagon House?  Christen your room with another bitter Christian?”  He tried out a devilish grin.  He was enjoying trying to find Cas’s boundaries and breaking points.

“I may indeed have designs.  Do I have to ‘call dibs’?”  Cas made air quotes.  Dean made a duck face and swatted Cas’s hands down.

“Save the dorky shit for your act.  And no dibs necessary.  I never commit this early.”  Dean checked his watch, chest puffed with his boast.  “Plus I’m less of a hunter, more the hunted.”  He jerked his head to the side, and Cas followed the nod to see a group of five college-aged women in full dance-club attire, ogling Dean as their most gossipy member furtively whispered his stats - length, girth, stamina, etc. into their open ears.  Dean smiled knowingly, without even looking, as five very determined ladies licked the sugared rims of their fruity margarita glasses in a predatory fashion. 

“Interesting.”  Cas mused, with a small tilt of his head.  “Will we be hosting a party later?”

“Yes.  And we’re carding everyone.  Your girl's giving me the creeps.  Not it on the first door shift!”  Dean put his finger on his nose, and his volume rose almost high enough to interrupt Meg’s routine.  The movement caught Sam’s eye, and he quickly followed Dean’s lead, poking the end of his nose with his own pointer finger.  Cas bowed his head to his fate, and turned his full attention back to the newest object of his lust. 

 

**Notes for the Chapter:**

> *https://www.chick.com/reading/tracts/0283/0283_01.asp  
> There's the Chick tract about David and Bathsheba for you. The raciest thing little home-schooled Cas could get his hands on. I feel his pain (lived his pain).


	3. Repeat performances

**Summary for the Chapter:**

> Life at the octagon house: gettin' chicks, babysitting toddlers and planning parties.

**Notes for the Chapter:**

> *to music*  
> Beeetter late than neeeeever.  
> Beeeeeeetter late than neeeeever.  
> Better laaaaateee-  
> Even greeeaaaat-  
> Better late than never late than neverrrrrr.
> 
> Life is a little bit 'balls' sometimes, you know?  
> **now with a few small edits that actually acknowledge Ben's presence throughout the entire scene.**

“Speaking of holidays-” a sober girl snorted at the fact that Gabriel was not at all just speaking of holidays- “what the hell happened to the Macy’s Thanksgiving Day Parade?” He gave the audience a theatrically appalled glare.  “I’ve watched that shit show every year, but I can’t tell you when it went from a couple of marching bands and a Snoopy balloon and became a full on _Broadway review_.” Gabriel sung and jazz handed out. He was very physical. “Seriously.  As a card carrying, flaming homo, I gotta apologize to all y’all. Because this three hour waving-Barbie-Menudo-concert they're calling a parade is clearly programmed specifically for the gays.  And I swear, we didn't ask for this  We have no great bubbling need for giant turkeys to be inserted into all of our favorite musical numbers. Macy’s is just super duper thankful for us.” He smiled so genuinely that it distracted the crowd from his beading perspiration.

“And I can tell you the last time I wondered how many trays of Stouffer's lasagna would fill the cubic footage of balloon Garfield’s stomach. It was never.  I don't know about you, but I’ve never had trouble interpreting the scale of a hot air balloon when it is travelling down a crowded city street. And if I were having an issue, I don't think frozen food would be my goto unit of measure.” Everyone laughed. Gabriel was well liked, and he was familiar.

Dean leaned on the bar in the back and begrudgingly decided to give credit where credit was due. Gabriel dragged his ass up on stage week in and week out and created the perfect atmosphere for comedy. Newbies could climb onstage after one of Gabriel’s intros, and the audience would give the kids a shot.  The man sold himself as a sex-crazed, flamboyant man-child, but goddammit, people trusted him.

“But I'm thankful for a lot of TV. It’s a comforting feeling, knowing that all of America is tuning in to the same thing. I feel connected to my countrymen. It's something I tell myself when I get road rage or encounter what seems like a giant asshole.   _You,? Encounter a giant asshole?  In Kansas?”_ He mimicked the voice of an anonymous audience member. “Oh yes, believe it or not, it’s happened.  And when it does I just say ‘you know what, Gabers? That guy could be suffering from the very same wet nightmares about Hannah Montana at a construction site as you!  He could wake up in the night in a cold sweat, with a boner, and have fleeting visions of a nude, underage girl and demolition.  We're all just people. And we’re watching the same tv. It's a beautiful thing.”

Dean looked around the bar. Cas had introduced himself to Meg, and seemed to be very stoically regaling her with stories of… the Octagon house, if the angles he was trying to portray with his arms were any indication.  She was wearing a perma-smirk and stirring her drink for no reason whatsoever. So yeah, Cas was getting laid. Time for Dean to get with the program. His eyes searched the crowd and honed in on Sam, shoved against the wall near the bathrooms as Ruby tried to eat his face. Everyone was shitting where they ate tonight, apparently.  Well that was fine with Dean, because Lisa had just wiggled her skinny ass onto the stage and started a string of yoga inspired downward dog jokes that fully featured her flexibility.

Dean knew Lisa was downward for whatever, because they had actually hooked up once a long time ago. Unfortunately, the next morning a run of bad luck at her apartment complex had forced her to ask Sam and Dean if they could babysit. Dean immediately liked her young son Ben a lot, so he had spent the next few weeks awkwardly trying to friend-zone Lisa while demanding to help with her kid.  It was a confusing time for everyone.  Finally she cornered him and assured him that he could help with Ben anytime without having to do anything heinous, like actually date her, though a quick wink at the end had suggested that she'd be okay with another no-strings-attached-liaison sometime.  But their hook up schedules had never synced up again.  It made sense. She was a busy single mom. But if the tall gin and tonic she had brought on stage with her was indicative of anything, this might be a good night for a second run.

………………………………...

The next morning Dean made pancakes at 9:45 as the sun streamed through the East window, which was right above the sink, deferring everyone from bothering to wash any dishes until after noon.  Lisa had left before the sun punched him in the face, Meg and Ruby hot on her heels. The women of Kansas comedy apparently couldn't quit their day jobs. Cas emerged from his room first in a blue plaid pajama set, scratching his chest where the top five undone buttons exposed him to the chilly air.

“So, how was your night?” Dean asked as he served pancakes, purposely chipper.

“Interesting.” Cas replied. He eased himself into a stool and picked up a fork.

“Just interesting?” Dean challenged, eyes searching Cas’s head and chest for hickeys.  Cas squinted at his pancakes like he wasn't sure if they were lying about having the nuclear codes, and were actually expendable.

“Meg is an enigma.”

“How so?” Dean pressed against the finality of every single statement Cas uttered, ever.

“She appears to be hiding a truly generous heart behind a facade of indifference, but then in the throes of passion she repeatedly referred to me as ‘Clarence’, and seemed to get a great joy out of suddenly ceasing all movement whenever I was close my climax. And she pinches.”

“Ah.”  Cas had given many indications that he was not shy about sex, so Dean just barely suppressed his urge to claim TMI.  “Who's Clarence?” Dean frowned.

“Who, indeed?” Cas said gravely, then bit into his breakfast.

“Ooooh, pancakes!”  Sam approached the kitchen counter in nothing but an old pair of grey sweatpants. “Thanks, Dean.”

“Yeah whatever.” Dean grumbled. “Go eat ‘em in your room.  You’re gettin’ Ruby stench all over everything.”  Sam rolled his eyes.

“Screw you.”  Sam yawned, and grabbed his plate, forgoing maple syrup because he was slowly transitioning into the spawn of Satan (the only plausible explanation for skipping syrup in Dean’s mind).  He plunked off back to his room and left Cas and Dean to finish alone.

“I’m sorry.  I’m being rude.  How was your evening?”

“Good.”  Dean tilted his head and considered his elaboration as he walked his dish to the sink.  “Lisa just keeps getting bendier and bendier.”  Dean didn’t really kiss and tell, but he didn’t want Cas to think his earlier comments about Meg had been too much.  For his part, Cas didn’t seem to notice

……………………………………………….

If Dean was worried about Lisa having a renewed interest in him, that worry was quickly squashed a few days later when she called and asked  if he could babysit Ben while she went to a golf benefit with some guy from work.  

It was a lazy, summer Thursday, and Dean was happy to sit around in the AC and mellow out with the kid for a while.

“Oh hey, Ben’s here.  How’s it going, guys?” Sam entered through the front door, clutching two brown paper bags that were definitely from the natural food co-op. Sam had been treating himself ever since Cas had eased some of their financial burdens.

“This Turbit guy needs to get his shit together.” Dean gestured at the colorful children’s program splashed across the flat screen.

“Dean.” Sam pulled his ‘disappointed mom’ voice.

“Relax.  He’s heard it.  His mom is Lisa.”

“I can’t say the “S” word but mom and Dean can.  But I can say “butt” as much as I want.”  Ben proceeded to chant “butt, butt, butt, butt, butt” as he wiggled his body over the arm of the couch, eyes glued to the television until he toppled onto a cushion on the floor, which pulled a delighted giggle out of him.

Castiel began pounding his fist on the coffee table in solidarity.

“Butt, butt, butt, butt.”

“Real mature, Cas, thanks.”  Dean gave him a wry side eye.

“It’s extremely invigorating to see a child getting reared with so much freedom of expression.”

Dean blinked hard, cringing at the sudden onslaught of feelings that would certainly besiege him if he bothered to make eye contact with the assumedly grimacing Sam. Cas continued to watch with rapt attention as Captain Turbit behaved amorously towards a walrus.

“Well.” Sam cleared his throat. “I'm gonna get my butt into the kitchen and make us some PB and J’s.”

“Butt!” Ben yelled.  Dean raised his fist in the air. Cas smiled at everything, without moving his eyes from the TV.

“Hey you guys busy tomorrow night?” Sam half-yelled from the kitchen.

“I gotta go to Ash's at 2:00. He just got a chicken plucker.” Dean called back, deftly fast-forwarding through a block of commercials while Ben yelled about his extreme hatred of ‘amershalls’.  Cas turned his head and gave Dean a serious stare. “What? They’re dead when they go in.” Dean added, defensively.  Cas furrowed his brow.

“Don't give him too much shi- ...shite for it, Cas. Free range chicken is over five dollars a pound in the stores, whereas Ash gives Dean at least five good-sized roasters just for helping.” Sam had money on his mind as he stowed away a $14 jar of organic cashew butter.

“I don't protest.” Cas was the king of sitting still, and he remained stationary now on his side of the couch. “I helped my adoptive father butcher many animals. I was simply trying to remember if I have a dentist appointment tomorrow, or if I can accompany you and lend a hand.”

“Well back to what I was trying to say,” Sam joshed as he dusted off his hands and approached the couch, “I've got some new material and I was thinking it's maybe about time we have a trainwreck.”

Dean’s eyebrows initially jumped to his hairline, but they quickly fell into more normal territory as an evil grin overtook his face.

“What is a trainwreck?” Cas asked, slightly annoyed that the definition was not automatically apparent or offered.

“Well,” Dean began, with a tone of voice better suited for Ben’s age group, “we host a big party,  we set up a microphone, we all get obliterated, and then we try to do brand new, never tested material.”

“Oh. That sounds appropriately named.” Cas looked thoughtful and intrigued.

“It's a really safe environment for experimentation.” Sam gushed.

“Okay, Madame Curie. I'm sure he can figure out what it's good for.” Dean leaned over to Cas and lowered his voice just slightly. “Doing all the raunchiest bits you can think of and using booze as your excuse.”

“Dean.”  Sam huffed.  “The point of the trainwreck is to test out material that you can actually use, not to make racist and culturally insensitive jokes just because you know your audience has like zero cultural diversity.”  Sam gave a disgusted shake of his head and headed back towards the kitchen.  Cas tilted his head and stared at Dean.

“I have no idea what he’s talking about.”  Dean told Cas with a serious deadpan.

“Oh yeah?”  Sam called from the kitchen.  “Then what would you call your 72 virgins bit, other than ‘embarrassing’ and a huge waste of time?”

“I would call it a work in progress- perfect trainwreck material.  You’re being a baby.”  He turned to Cas and pointed at the kitchen.  “He’s being a baby.”  

“Okay, listen to this, Cas.  Listen to this and tell me it’s not ridiculously inappropriate.”   Sam had stomped back into the living room, wielding a spatula like a scepter.  He crossed his arms and looked at Dean, tapping his foot when Dean didn’t immediately launch into the demanded routine.

“I’m not gonna-”  Dean tried to find a resting place for his hand for a moment, awkwardly.  “No.  Tell him yourself if you remember it so well.”  Dean stuck out his chin, one hand finally landing on his waist.  Sam mirrored the defiant chin, and turned to face Cas with a noticeable amount of his ‘performer’ swagger.

“Alright, so as absolutely _hilarious_ as it is to bring up radical suicide bombers, that’s how he begins.”

“That’s not how it starts.” Dean interjected.

"I can't hear my SHOW."  Ben interrupted.  Without acknowledging the kid, they all dropped the decibel level a considerable amount.

“Even though he totally knows better, he plays on the status quo generalization that all Muslim people are radical and sexist.”

“Look, the stories of martyrs getting awarded 72 virgins are reported to be the reason anyone does any of that suicide bombing crap.  Just like we know AIDS started when a guy had sex with a green monkey in Africa.” He adds, sarcastically, then mimes wiping his hands clean.  “It’s the media’s fault, not mine.”

“Dean, you’re supposed to be making fun of America’s willful ignorance, not relying on it.”  Sam slumped his shoulders.

“I relied on nothing.  It was trainwreck.  And there was seriously no context.  I said ‘You know what sounds like the worst thing ever?  Finding yourself in a lush paradise with 72 female virgins.’  I brought up how the male need to devirginize things was totally illogical.   I said that if I want to put the moves on a beautiful woman, I didn’t want to have to precede it with a sex-ed class.  Let alone 72 of them.  Or would I only need one, because we’d have 71 other virgins looking on with interest?  Is that my job now?  Teaching young women to screw?  What if they all don’t want to?  Statistically, some of them are bound to be gay.  But honestly, where did they come from in the first place?  Did they live on earth and die a virgin?  Because there’s usually pretty specific reasons that people die without experiencing sex with another person.”

Cas’s head had tilted to the side, and while his eyes looked questioning, he was having trouble hiding a smile.  Sam rolled his eyes in annoyance, catching a glimpse of Cas’s smile and shaking his head as if they were all lost causes.

“What do you think, Cas?”  Dean asked in earnest.  Cas licked his lips and squinted at the ceiling.

“I’m afraid I’m not the most objective party, considering my act is primarily jokes that mock the ridiculous notions of my extreme Christian upbringing.  I would hate to say that the inane ramblings of any one religion should be untouchable to comedians.”  

“Ha.”  Dean lunged his head towards Sam so that Sam could feel the breath of his triumph.

“Think of it this way.”  Cas counseled.  “It wouldn’t be nearly as funny if society had less uptight feelings towards sex education and the exploration of one’s sexuality in general.”  

“Whadya mean?”  Dean asked.

“The idea that virgins can’t be educated and in tune with the likes and dislikes of their own sexual organs.  Or female virgins, at least.  No one questions whether virgin males know what they want out of sex.  It is ultimately a commentary on sexism in our perception of human sexuality.”

“Double ha.”  Dean shimmied his shoulders and wiggled his hips in a bizarre dance of triumph.

“Whatever.  You’re supposed to be a professional.  You could find a better way to make a ‘hilarious’ commentary on sexism in our perception of sexuality than using an inaccurate reference to the scriptures of a religion that most practitioners are currently persecuted for practicing.”  Sam’s lip nearly curled as he muttered his protest, nose wrinkling at the spastic movements of his brother.  Cas looked to Dean with his _he’s got a point_ face.  Dean stopped his jig, and scowled.

“Okay, okay.  I ditched it anyway.  You win.  Now please, continue to regale Cas with stories of how great a trainwreck is for experimentation.  I’m calling Ash.  Not it on door duty.”  Dean quickly put his pointer finger on his nose.  Sam echoed the motion, then turned an evil smirk to Cas, who looked befuddled.  Even Ben reached up and made his nose into a pig snout, his eyes still glued to colorful children's programming.

“Will this be how we decide everything?”  Cas reached up and put his finger on his own nose.  Dean reached forward and swatted it away.

“Suck it up, man.  You lost.  Means you gotta ID everyone that comes in and make sure they’re over 21.”

“Hmm.”  Cas pondered, looking unruffled by the news that he would be playing doorman at his very first trainwreck.


	4. Trainwrecks

**Summary for the Chapter:**

> They're so drunk, it'd be more accurately called 'slouch-up' or 'attempt-to-stay-standing-up'. Amiright?

**Notes for the Chapter:**

> My notes at the end are psychotic. **So I deleted them! Yay! That leaves a few comments on this chapter not making sense. I don't think this will bother anyone, but if it does, the long and short of the notes were me blathering over whether it can somehow be considered to be "wrong" to write porn about characters who's physical vessels are the real-life transport of hot actors. I was told. We can all move on.

The Trainwreck was underway, and nobody could help but rubberneck.  The bottom floor of the Octagon house was a sea of drunken comedians and their friends.  Bedroom doors were closed and locked.  The key to the bathroom was a hot commodity, and there was a fine mist of Pabst Blue Ribbon on every laminate surface of the kitchen.  

The strange rhomboid-ish shape of their communal interior all culminated in the living room, which had a milk-crate and plywood stage set up, with one microphone and a two speaker PA.  The system really cranked, so there was nowhere you could go to escape from the comedy, though someone had set up a little bluetooth speaker with a hipster party playlist in the kitchen to bridge the dead-air between performers.

Castiel was standing at the front door, dutifully, if not a little bit high to take off some of the sting of having an assigned vocation during a raging party.  On a more positive note, he had carded a young man named Samandriel early in the evening, and thanks to the child-like creature being a legitimate 22 years old, he’d been eyeing him like a rare steak all night.  In return, Samandriel managed to look shy, innocent, and eager to flirt all at the same time.  Cas’s mind whirred through possible comedy material that might be useful to woo the gentleman.  He tried not to be distracted by the fiery red-headed girl up on their “stage” who was playfully self-deprecating herself for being a geek whenever the listeners didn’t seem to get her references.

“So, do you ever have one of those days…” her voice had a lilting quality, but she somehow smoothed over the higher frequencies with a childlike timbre.  “It’s like, you wake up in the morning and the alarm gives out a warning.”  Gabriel’s tell-tale snort sounded in the front of the listening crowd.  Castiel wrinkled his forehead.  Gabriel was always the first to “get” any joke, especially ones that referenced bits of pop-culture that Castiel had missed out on during his childhood of Christian slavery.  “And you just don’t think you can ever make it on time?”  Charlie looked around, grinning.  This was not the crisp and efficient routine that Cas had caught at the Laugh Shack.  This was meandering, possibly drunk, definitely high Charlie.  But her sober self had anticipated it, and set up a camera in the back of the room to record her loose lips for future entertainment purposes.

“You know why it’s so expensive to have a dog these days?  Because kids can’t supplement their diets with homework anymore.”  She blurted out.  “‘Cause everything’s digital.  Amirite?  Thank the Force for that.”  The members of the trainwreck audience were all holding red plastic cups, and they were radiating clouds of positive energy that smelled a little like a skunk.  They laughed.

“Zack Morris.”  She mused with a sigh.  “Zack mother-fucking Morris.  Who here didn’t want to be Zack Morris?  Mm.  He had the hair.  He had the girls.  The administration was wrapped around his finger.”  She twirled her pointer finger.  “I would seriously give up my entire history with the Xbox to get wrist-deep into Kelly Kapowski, holy Jesus.  She could kill my dick any day.  Hell.  I’d hack a bank across state lines and buy a dick if Kelly Kapowski wanted to kill it.  That is a dick killing lady right there.  Dick ninja.”  The crowd was about 75% male, and they were on board with everything - lack of coherent storyline and all.  

Castiel was puzzled, but overall had gathered that Zack Morris was an All-American type TV character who had a very desireable, Polish girlfriend whom Charlie and the rest of the audience really wanted to diddle.

“Ugh.  I’m so gonna regret this tomorrow.”  Charlie leaned heavily on the microphone stand and shut her eyes as if to try and stop the room from spinning.  Sam hopped up and rescued her, patting her on the back and guiding her down the one steep step to floor level.  She smiled up at him gratefully.

“That was Charlie, everyone!”  Sam leaned over to slip that into the microphone before guiding Charlie, his heavy hands on her shoulders, towards the kitchen.  People cheered.

“This is Kelly Kapowski.”  Dean’s voice next to his ear made him jump, but recreational drugs allowed him to internalize it.  He turned his head, slowly to find Dean holding up his cell phone with an image of a very pretty girl with a very dated fashion sense.  Cas smiled at Dean, who had known that Cas was in the dark when it came to most of Charlie’s ramblings, and had come over to educate him.  

“I’d ‘hit that’.”  Cas responded, using his finger quotes because they always made Dean smirk.

“Dark hair.  Green eyes.  Hell yeah.”  Dean took one last look before putting away his phone.

“Like if you and I had a baby.”  Cas added.  A giggle erupted out of Dean before he could squash it.  He looked at the floor while Cas just looked placidly pleased.

“You’re such a fucking weirdo.  You got more than a contact high going on?”  Cas did, enough so that he couldn’t ascertain why Dean would ask.  Quizzing people about their level of indulgence had become firmly ingrained into their culture of debauchery by Sam and his “Social Justice League” (as Dean fondly called it) so questions about consumption were beginning to be interpreted as flirtations.

“I am coherent enough to give informed consent, if that is what you're after.”  Cas answered, adding a slow wink. Dean gave him an odd look.

“Well that’s just peachy.  How ‘bout you consent yourself up to that microphone and help make some trainwreck history.”  Dean put his hand on Cas’s shoulder and gave him a gentle nudge towards the stage.  The comings and goings at the front door had quieted down quite a bit, but Dean answered Cas’s questioning look with a nod to indicate he’d take Cas’s place.  Cas smiled and bounded towards the stage.

“I didn’t really have a lot planned for tonight, so I apologize in advance.” Cas rolled his head around to loosen his neck, then snapped up straight to address the audience.  “Has anyone here ever milked a goat?  Show me your hands.  No?  No hands?  Well then let me tell you about it.  The first time is...exhilarating. First rule of goat milking - locate a lactating female. ”

Dean smiled as the audience snorted and guffawed.  Cas likely wasn’t aware of the backlog of gross-out comedies that pulled the oops-I-just-milked-a-bull gag, but he moved smoothly on into a very literal description of goat reproduction that’s only comedic device was absurdity and a general lack of understanding on the part of the listeners.  He had a way of  making things his own.

Cas, for his part, visually checked in on three people over the course of his act:  Sam, Dean and the bright-eyed Samandriel.  Sam’s very expressive face was like a lighthouse that metered and broadcast the success of his material.  In contrast, making Dean laugh despite himself was simply a guilty pleasure, and sometimes far too easy.  Dean would cough out a chuckle, which would cause his chest to heave, knocking his crossed arms apart, which would leave them swinging awkwardly for a moment as he smiled at the floor, then automatically rebuilding his tough-guy posture and leaning on something with all the allure of an underwear model.  Samandriel, well he was a tough nut to crack.  The boy laughed at the right places, threw around shy but smouldering gazes, and seemed to be focused solely on Cas, despite the respectable number of available women in the audience.  All good signs, except for the fact that Castiel was referring to him as “the boy” in the first place.

“I know my subject material tonight has been a little odd, but I’m not worried.  Coming into the secular world as an adult, I was delighted to learn that I’m free to talk about almost anything.  Blasphemy, anal beads, anal sex,  dildos, gun violence, sadomasochism, substance abuse, LSD trips, that thing where adults dress up in mascot costumes for sexual reasons…”   

“Furries!”  A female voice making a great effort to sound lower than it really was yelled out from the back of the room.

“Thank you.  Furries.  Right.  As of yet I’ve only discovered one taboo subject in all of modern popular culture.”  Cas paused as everyone looked at him, expectantly.  “And that’s my time.” He grinned, and gestured apologetically toward the back of the room as if to imply that someone had given him a signal to leave the stage.  This prompted the audience to render the appropriate groans and applause.  He smiled, and made his way towards Samandriel.

“Hi.”  The boy said, with just the smallest twinge of hero worship in his big brown eyes.

“Hello, Samandriel.”  Cas responded, oblivious to the idea that stealing someone’s first name from an ID card was a tad creepy.  Samandriel blushed.

“It’s Alfie.  I mean, you can call me Alfie. It’s a middle name nickname.”  He blushed a little, and coughed.  “Uh, so what’s the one taboo subject?”

“It’s menstruation.” A sharp, feminine voice ploughed into their conversation, followed by the tipsy form of Meg Masters.  “We totally had this debate the other day.  Periods won, hands down.”

Castiel smiled at Meg, because this was all true, and because he was not socially savvy enough to realize that a former one-night-stand falling into conversation with your future one-night-stand was any reason to panic.  

“Hi I’m Meg.”  She placed her hand out for Alfie, who managed to free his corresponding hand from his black and red windbreaker pocket and shake, timidly.  “Oh you are fucking cute as a button.”  Alfie blushed and began to stammer.

“I’m sorry, I’m - um, thank you.  I’m just kind of mostly, like 95% gay?”  Alfie looked to Castiel for some kind of confirmation.  Castiel smiled a friendly smile.  Meg bounced it back to Alfie like a fun-house mirror.

“Oh, baby face, I can tell.  And you’re lucky my uterine lining is madly evacuating my body, or I’d be working very hard to be a five percenter, with the help of Clarence here, and a god-awful Britney Spears song. Or Blind Melon. Your pick.”  Alfie blushed some more, which seemed to be his go-to move, while Cas looked at the ceiling as he filtered through everything he knew about Britney Spears.  “But as it stands, I’m just here to give Castiel here his bedroom key, if he wants it.  She tilted her chin down a little and smirked at Cas through her lashes.

“Why do you have my bedroom key?”  Cas asked, sincerely.

“It’s a good story, actually.  My friend Bella wants to screw Dean Winchester silly, and apparently Sam is tonight’s Keeper of the Keys.”  Cas and Alfie just blinked at her.  “He’s also a little drunk.  She stole Dean’s, so I stole yours.”  

“Why?”  Castiel asked, genuinely while Alfie shuffled his feet in discomfort.

“Meh.  I was thinking I’d suck you off, but you’ve got this whole eye-sex thing going with Leave it to Beaver here, and I’m getting to the point where I just want to drown anyone who talks to me in Cadbury cream and then cry on them. So, blow job averted.”  Meg cheered her hands into the air, half-heartedly.

Cas wondered who Richie Cunningham was, then pivoted to gauge Alfie’s reaction.  He didn’t realize the Octagon house had any sort of key/ permission system, but this promiscuously blatant introduction was a surefire way to acquaint Alfie with the style of somewhat meaningless physical gratification he was about to potentially embark upon.  He turned to the boy and looked deeply into his eyes.

“Would you be interested in finding out how many walls my bedroom has, and also some form of sexual relations, with me and only me?”  He gave Meg a little glare at the last part.

“Uh.  Wow, that was easy.  Um, Yes please.”  Alfie answered, unconsciously licking his lips.

“Here.”  Meg held up the key, and Castiel reached out for it, only to have her pull it away a moment later. “Well, maybe I want to watch.  Can I watch?  No, ‘cause I have to drive Bella home.  Fucker.  Okay, nevermind.  Rain check.”  She offered the key to Cas once again, and he retrieved it quickly this time.

“Rain check.”  Cas repeated, politely.

“Actually  I’m just visiting my cousin Garth for the weekend.  I’m actually from Idaho.”  Alfie added, earnestly.

“Gaaa.  Fuck my ovaries!”  Meg growled at the sky.  “Now get out of here, you crazy kids.”

Cas shook his head in mild disapproval, then took Alfie’s hand and pulled him gently through the crowd until they reached his bedroom. He fumbled with the key a little, finally getting them safely locked inside. He flipped the overhead light on, then winced, and stepped to the bedside lamp, clicking it on and the overhead switch off.  They were then gently swaddled in a dim yellow light.

“Hmm.” Alfie hummed as he unzipped his windbreaker and shrugged it onto the floor. “One.” He took Cas’s hands and began twining their fingers together, pointing his little nose at each wall as he continued to count. “Two, three, four,” he stepped into Cas’s personal space and pushed the older man’s back up against the fifth wall with enough oomph for a light thud. “Five.” He reached his mouth forward and caught Cas in a hungry kiss, pushing Cas’s hands against the wall in a surprising, but not unwelcome show of dominance. Cas kissed back with vigor, though Alfie’s tongue was skittish and quick, pushing the pace a tad faster than Cas would have usually enjoyed.  

The younger man suddenly pulled back and reviewed his handiwork, and Cas must have looked sufficiently taken by the kiss, because Alfie promptly dropped to his knees and unsheathed Castiel, immediately moaning that his cock looked delicious.

Cas tried very hard not to start formulating a joke about the amount of blind trust it takes to let a virtual stranger suck your cock.  But seriously, this kid was full of surprises, and ever so nonchalantly breathing on a very sensitive organ that Cas only had one of. Luckily, Cas happened to enjoy the way his heart began to race, pushing his residual performance Adrenalin out into the tips of his ears and the nails of his toes.

Perhaps it was a symptom of his youth, but Alfie only let the anticipation build up for a moment before he set to work, licking and sucking and performing fellatio as effectively as one can on a buzzing stranger.

Cas set about trying to enjoy the experience. Through the wall he could just barely hear the telltale creak of Dean’s bed, interspersed with pizzicato points of a female voice.  He was just drunk and high enough to start building a mental image of what Dean was getting up to next door with this Bella character.  Dean was teetering on the line of bulky when it came to his musculature, which likely put him on the bottom of his random hook-ups, just for the sake of less intimidation.  Cas had carded Meg’s friend Bella at the door, and he remembered her being petite.

Alfie began to moan for attention, and Cas remembered where he was.  He carded his hand gently through the boy’s fine hair, looking for a response.  Alfie simply lifted his eyes to give Cas a smoldering glare.  Cas arched his hips forward just slightly, and didn't miss the flinch of annoyance in Alfie’s forehead.  But he wished he had, because that was a truly pleasant sensation.  

Dean's bed thunked against the outer wall of his room, which caused Alfie to pull off with a deer-in-headlights look.  

“Did someone knock?”

Cas looked down at Alfie’s concerned expression, obscured slightly by his free-bobbing penis, and overall, the moment left something to be desired.  

“Don't worry, the door is locked. You heard my roommate’s bed. Clunking.”

“Oh.” Alfie swallowed, a grin blooming in the corner of his puffy pink mouth. “Guess that means they could hear us clunking, huh?”

“Yes.” Cas mirrored the expression, suddenly optimistic about the remainder of the encounter. Maybe before he was offput by the youngster taking the lead so quickly. Whatever the case, he ran with the knowledge that Alfie seemed turned on at the thought of being heard, groaning with exaggerated gusto when Alfie leaned forward to lick up the length of his cock.

………………………………………………………………………….

“Ooh. Sounds like your neighbor’s getting lucky.” Bella purred into Dean’s ear.  They had ended up with him sitting on the side of his bed, her writhing around on top of him in a manner that would have been far sexier if it didn’t cause her long, soft locks to brush back and forth over his nose. There was nothing sexy about scratching your nose, but it was all Dean could think about at that moment.  Bella suddenly twirled off of his lap and sat next to him on his bed, slowly unbuttoning her white, collared tank top.

“Up.  Strip for me.”  She ordered, her posh accent and nonchalance pairing to make her sound like a strict British nanny.  So far she was proving to be a bossy little bedfellow, but Dean had no complaints, more appreciative of too much talking over none at all.

Dean’s body followed the order, while his face paused to question, and his eyes went to examine the lacy white bra now exposed by Bella’s open blouse.

“Like strip, strip?”  He wasn’t about to go all Magic Mike on a stranger without some clarification.  He hitched his thumbs on his belt buckle and turned on the good ‘ole American boy swagger that Bella seemed so enamored of after only a few moments of conversation.  Bella reached into her pocket and pulled out two one dollar bills, waving them at him with a smirk.

“Don’t keep me waiting.”  She chided.  Dean got down to business.  

He began to slowly move his weight from one foot to the other, adding a small hip pulse, and watching Bella’s reaction closely.  She noticed, and focused her gaze greedily on his crotch.  The rhythmic hip pulse got a little snappier, almost on its own accord.  Dean slid his hands smoothly down his torso to the hem of his henley, pulling it up over his head with a whoosh, and tossing it towards his laundry hamper.

“Ooh yes.  Take it off, cowboy.”  She shrugged out of her shirt, almost unconsciously, and pulled her knees under her, so that she was kneeling on the edge of his bed, topless and enthusiastic.  Dean smirked, and shimmied his way a few steps back to his closet, reaching a flexing arm in slowly, and bringing it back to reveal a dusty cowboy hat.  Bella clapped and hooted as he bowed his head down to curl the hat onto his head.  He then gave her a wide-eyed wink. She giggled, and made a show of sucking on the tip of her pointer finger and sliding it down into her bra to caress her own nipple. Dean was immediately jealous of that finger.  He began to lose the imaginary beat that had kept him gyrating.  Bella noticed with a pout.

“Why don't you get over here and show me what your packing?” She suggested, while pressing her hand down her stomach and under the waistband of her jeggings, then roughly curling her fingers into her soft tissue, and wincing in pleasure at the sensation.

When she opened her eyes she was greeted with Dean’s crotch, covered only with the tight fabric of a navy blue boxer brief, being flicked towards her face at a dizzying speed that caused his abs and lats to flex and glisten with the effort.  She pursed her lips and blew on the bulge, which Dean couldn't really feel, but the visual made it worthwhile nonetheless.

Bella shimmied out of her pants, standing up on Dean’s bed and leaning a hand on his shoulder for balance. Her lace-trimmed beige panties had a small smudge of moisture where she'd dipped her fingers into her wetness.  Dean tilted his head back to smile up at her from under his Stetson, then scooped her up like a true exotic dancer, grasping her ass firmly so that his cock was pulsing against her panties with just a tad too little pressure.

 

He stepped them forward, running his knees into the mattress and pitching forward enough for Bela to be dumped out of his arms, his hands catching her panties and tearing them up off her legs as she effectively fell out of them.  She squealed.  He reached to his dresser to grab a condom and stripped out of his briefs, while Bela unclasped her bra and sent it soaring across the room.

It was at this moment, the application of the condom, the surrender to the bureaucracy of modern safe sex that Dean heard a moan come wailing through his wall that was neither his neighbor, Castiel, nor was it female.  Dean's overactive brain slowed time once again.

_Well shit. Cas is actually with a dude. He said he was down for both sexes, but honestly how many single gay guys are even in Kansas? Well that's something. Good for him._

Dean strained his ears a little to listen for corresponding moans from Cas, but the noise seemed one-sided. Meanwhile, Bela was nearly ready to start drumming her fingers on the wall in impatience. Oh well.  Bela's eyes were burning through his pectorals in what could only be described as a come-hither glare.  Yippy kai yay, motherfuckers.  Worrying about what his roommate looked like in flagrante with another guy would have to wait for another day.  It was now time to take the matter at hand and make it the matter at cock.


	5. Misplaced Europeans and Women have it rough

**Summary for the Chapter:**

> Dean does comedy!  
> Cas stares.  
> Meg is perceptive.

**Notes for the Chapter:**

> Hullo!  
> There comes a point when one has to look at one's writing and admit, I can stare at it all day, but it ain't gettin' any better. I have come to that point with Dean Winchester's comedy. Hope it's enough. Not 'good' enough or 'funny' enough. Just enough.

The morning after Castiel’s first trainwreck found the living contents of the Octagon house sated, hungover, and alone in their beds, except for Sam who woke to a blanket of Charlie, drooling onto his oversized sleep shirt.  They began to converge in the living room around 10, groaning and moaning about their water-starved muscles.  The sticky mess of the living room floor went unaddressed until after 12, when Sam couldn’t contain himself any longer, and began to collect empty cups and cans, dropping them into a white plastic trash bag he seemed to pull from his back pocket..  Cas was draped over the couch, his forearm covering his eyes, while Dean slumped in an easy chair with his laptop on his lap.  

“Ugh. I’ll help you.  Give me 20 more minutes.”  Dean grumbled as he watched Sam gingerly bend over to snag a cup.

“If you can wait even longer, I will hire a cleaning service.” Castiel groaned.

“I’m not passive aggressively telling you guys to clean.  I just want to get started.  Don’t freak out.”  Sam ordered, in his deliberately quiet voice.  Dean ignored it, as you must when one of your roommates starts tackling a mess that is everyone’s problem.  Cas valiantly rolled his body off the couch, landing on his hands and knees and wincing as if he were working hard to hold something in.

“You okay there, buddy?”  Dean tapped him between his shoulder blades as he suppressed a dry heave. “You had a big night.  You sore?”  Dean attempted to make the question sound casual, but it managed to catch Sam’s attention.  His brother narrowed his eyes at Dean.  Dean gave a jerky shrug and a glare back to Sam, to let him know he had no idea what the protocol was on offering up sympathy if indeed Cas were a bottom.  Sam let his head fall to the side in a typical  _ are you kidding me? _ Glare of incredulity, followed by a questioning shake of his long locks, which Dean interpreted as,  _ do you go around asking girls if they’re sore the next day?. _  Dean threw his head back into an annoyed, silent groan.  When he righted himself he went all in with a  _ I’m asking ‘cause I care, so back off. _  Meanwhile, Cas had been panting, until Dean felt his back raise up under his fingertips as Cas used the bench of the couch and then the armrest to help him become vertical.  Sam looked Cas over, sympathetically, letting his silent criticisms of Dean’s wording fall to the wayside.

“I am sore.”  Cas stated, plainly, rubbing his eyes as if he’d just woken up again.  “I forgot how physically dense men can be, even the thin ones.  I think I may have pulled a muscle in my lower back.”  Dean’s hand had felt oddly compelled to keep contact with Cas as he stood, to be ready for any sudden emergencies. The lower back was where it had come to rest, until Cas cited the area specifically, at which point Dean quickly dropped his hand to his side.

“You’re gonna have to start lifting with me and Ash.  All that running can actually eat away at your muscles if you don't strength train and eat right.”  Dean used his dude-bro voice, knowing Sam was rolling his eyes at him for sounding like a meathead.  Cas managed a smile, then strolled purposefully to the kitchen, back straight, hand on his hip, only willing to help clean things that were at a counter-height.

………………………………………………………………………...

Life at the Octagon House progressed steadily, as Sam, Dean and Castiel all became more accustomed to each other’s lifestyles, while also making very slow progress towards becoming established comedians.  Dean got a gig opening up for a comedian who had her own show on Comedy Central.  He was booked on two stops of her university tour, and he was proud to say that his act went over well.  She was proud to say “I totally hit that!” whenever anyone mentioned Dean Winchester, so it worked out great for everyone.  So great, in fact, that one of the organizers of the tour began booking Dean for other shows in and around Kansas.  And that is how “the gang” was introduced to Fergus Crowley, a nomadic Scotsman who could do more pompous grandstanding with a heavy black wool coat and a smartphone than Donald Trump managed to pull off with a fleet of helicopters and a weave made of only the finest locks of ginger baby hair.

Crowley didn’t have an official title.  He was a small-time sleazeball trying to fill big-time shoes, which he believed meant never painting himself into a corner when it came to committing to any one interest.  Except for the interests of “his artists”.  He was decidedly against caring about those, ever.  On any given day he’d go from Manager to Producer to Booking Agent in the course of one too-long, innuendo-laden phone conversation.  His name in Dean’s contact list was “Necessary Evil”, but the booking calls started to trickle in more consistently for Dean, and occasionally there was room for Sam on the roster as well.  

It was around that time that Sam and Cas noticed that Dean’s act began to change a little with the added attention.  Maybe it was the sudden exposure to a couple hundred virile and idiotic young boys at a time during his college stops, but for whatever reason, his act began to lose some of its “bro” qualities.  He was getting older.  He was entitled to a little maturation.  It would be a lie to say that it didn’t make Sam a little emotional to see his brother morph into something a little wiser, but a little darker, right before their eyes.  Even Cas noted the new act with the deep, prideful sigh of person who was happily on the precipice of losing something intangible.  He was at least warmed by the fact that Dean had remained as goofy and stupid-pun-loving as ever in the privacy of their own octagonal home.

…………………………………………………………………………

Dean stepped lively onto the stage of the Laugh Shack, skirting a little so as not to run over the retreating MC.  The stage was lit with a harsh spotlight, and decorated with only a painted plywood signboard bearing the Laugh Shack logo.  It was a simple bar, and normally it was their Cheers, with no real introduction required for repeat performers like Dean, but tonight there was some sort of convention in town that had brought in about 20 new audience members, dressed up, but looking a tad blue collar, ranging in age from about 30 to 50.  It was a Saturday, and Gabriel had asked Dean to headline, specifically.  He had even arranged for his friend Balthazar to come up from Wichita to act as MC.  Balthazar was yet another misplaced European, stranded in the center of the U.S.A. by a bad relationship, and an even worse credit history.  But he was tall and his accent was alluring as fuck, as if the Queen’s English were his second language.  Gabriel liked to call him in for special occasions, to lend the night’s performance an air of officialism.  Gabriel said it brought out the best in everyone.  Gabriel had a thing for Balthazar.

Dean surveyed the crowd with a self-satisfied smirk. On stage was the only time he let himself acknowledge the power of his handsome features.  Since the beginning of his career, in that moment when the lights first hit him, there was always a flurry of fight or flight in his chest, no matter how comfortable he felt with the audience.  He'd stumbled through years of hit-or-miss performances, focusing so hard on crafting a comedic personality, looking to find that secret formula; one part whimsy, two parts self deprecation, and a pinch of naivety.  But the same jokes would pass as much as they failed, until he finally worked up the courage to chuck out the false modesty and wield his beauty like an ape waving a weathered bone at a monolith.  He was the manly, beautiful Dean Winchester. Hear him roar, then pick apart your preconceived notions about what beautiful, manly men should be thinking about life, the universe, and everything.

“Women, am I right?” Dean started.  Men looked up at their female dates, with a twinkle in their eyes.  They supposed this was gonna be one of those comedians that ruffled their ladies’ feathers.  So what if he was a little too good-looking?  He was clearly about to launch into some bitter rant about his dim-witted and superficial ex-girlfriend.

“Boy did they get a shitty deal.”  Dean licked the corner of his pouty mouth, and watched the front row wonder where he could possibly be going with this.  "Like, in politics, there's no ‘make America great for women,  _ again _ !’ campaign because there’s nothing to go back to.  We would be making a first attempt.  And so far, no one’s even ready to try for number one.”  He bit his lip, and reached through his legs to slide the tall wooden stool up under his butt.  “Come to think of it, when exactly was America so great- like greater than right now?  'S Stupid.  That is a stupid campaign slogan."

“You ever hear an old white guy politician warn people that if you elect his opponent who is a woman, she’s only going to worry about women’s issues?  Is it me, or is that guy flat out admitting that all that men in office worry about are men’s issues?  It’s not just me.  I got history to back me up.”  He let his back  hunch a little, feeling the moisture start to gather in the tightest pulled creases of his denim jacket.  The ability to camouflage any visible sweat was worth it, and that jacket had some badass James Dean lapels.

“How great would America be if we suddenly elected every single politician through a lottery process- like jury duty?”  Dean gave the audience a gleeful smile, then rearranged himself on his stool, and paused to ruffle the sweat through his hair.  “Hey, Dean, why so glum?”  He changed his cadence, firing words a little quicker and more nasally, while jokingly addressing himself.  “Aw man, I just got summoned to be Secretary of the State.  Shit.”  He wiped his hand down his face, stroking his cheeks in mock concern.  “I gotta find a way out of this.”  He shook his head in forewarning.  

“So then, like jury duty, you’d go try to get declared ‘too crazy’ to be in office.”  He looked up for a moment, pulling at the memory of his notes.  “You know, how everyone pipes up if you talk about jury duty, and they’ve got that list of declarations that they swear will get them out of it? And it’s SO important for them not to be involved in their civic duty that they’ll go into a public building and tell awful lies about themselves?  I’d be that asshole.  Because that’s how much I would want to distance myself from being a politician.”  He reached out to take a sip of his water, wiping his mouth on the back of his hand.

“But for politics, those easy outs would never work.  You’d be like ‘first off, I’m a total racist.’ and there’d be some bored counsel lady, like ‘you wouldn’t be the first’.”  Dean mimed checking something off on a clipboard with a very blase attitude. “Then you’d try again - ‘I hate women, and I don’t think any of them should work.”  Dean’s eyes darted all around with a hectic worry. “And she’d be like, ‘Oooh.  Shocking’.”  Dean droned in his most monotone voice.

“At that point I’d be starting to sweat bullets, because I know jack shit about foreign policy.  But, hey, that’s great, right?  Maybe I can stop lying about being a bigot, and  just tell them how inept I am!  ‘Excuse me, Miss?  I just realized, I have no idea where Gaza is, or if it’s a strip mall or who runs it, or what.  What can I say?  I’m a hopeless case’.”  He hopped up off the stool to explain his ignorance to an invisible party, offstage, then twirled around to face the opposite direction. “‘Oh really?  In that case we’re going to have to pull a second name and hold an election.’ And I’d be relieved, because who would vote for me, right?”

A “Wooo!” burst forth from a table of girls, and Dean smiled and winked at each one of them, individually, with just one twitch of his eyelid.  

“I got one vote.”  He quickly licked his left eye tooth, with an open-mouthed grin.  “But then my opponent would be this 65 year old lady from Tulsa, Oklahoma named Ruthie.  And she’d be just as much against becoming the secretary of state as I am, so we’d be airing out our dirty laundry at all the debates.  Ruthie would admit that she cheated in high school geography, and I’d admit that the bulk of my world history knowledge comes from Assassin's Creed and old episodes of Saturday Night Live.”  Dean shrugged sheepishly at the audience, who laughed because it seemed truthfully funny.

“But then preliminary polling numbers would come in and Ruthie would have a slight lead, and  we’d suddenly get competitive.”  He crossed his arms, leaning the microphone just under his bottom lip, and narrowing his eyes.  “Then we’d start fighting dirty.  I’d say the only reason Ruthie had the lead is because all old people do is vote.  Far as I know, it’s the secret to longevity.  Voting.  That's it.  Ruthie would have her Red Hat’s giving out homemade pie.  I’d take the pie.  I’m not above it.  I love pie.  I’d hide a whole one in my trunk."  Dean’s hand ever-so-gently caressed his stomach.  Cas looked on from his seat in what was essentially the fourth row, and wondered if Dean even realized he had reached for that area upon the mention of pie.

“Then Ruthie would fire back at the younger generation and how we’re just fucking and drunk all the time and we’re not good for anything.  So I’d tell everyone that she and her husband were addicted to edibles, and that’s why no one has ever seen Ernie awake for more than ten minutes at a time.” Dean paused to giggle at his own far-fetched imagery.  About 20% of the men and 70% of the women in the audience secretly swooned. Only certain comedians could pull off laughing at their own jokes. Dean was blessed.

“Our final debate would be like a UFC weigh-in.  Dana White would have to be in the middle, keeping us apart.” Dean waved his arms, stiffly between two invisible opponents in his best impression of the UFC’s president.  “Ruthie would be yelling old-timey nonsense and I’d be yelling right back, ‘this is one secretarial position that you’d better let a MAN handle!’ and the crowd would go ‘OOooooooh’ because that’s just low.  I should know better. But I would have gotten carried away.” He hung his head, letting his voice drop an octave in shame. “And now, the win is right there, and I can fucking taste it, and it's making me crazy. Ruthie might make a mean strawberry rhubarb, but she's going down.”  He held out his hand to grasp the invisible title in his fist, forearm rippling in the spotlight, to the delight of many.

Castiel was one of the many, in this case. He played with the zipper of his maroon hoodie as he tried very hard to not to let his mind go off on a tangent regarding Dean’s forearms.  He failed, and had soon followed the obvious trail of anatomy to begin reviewing Dean’s propensity for gentle, supportive touches. Yes, both Winchesters were tactile in their friendship, but Dean tended to let his digits … linger wherever they fell. His hands were free to continuously caress until the moment someone directed conscious attention to them.  Castiel had always had a hard time containing his glare when anyone did as much.  

But thinking of Dean this way could pose a problem.  Castiel was kind person, but purely interested in physical pleasure when he fell into bed.  He had a gaping void where his family should have been, but he had filled it with safe sex, comedy and friendship.  He didn’t need any sense of yearning screwing that up for him, especially if said yearning was simply for Dean to run his thick fingers through Cas’s hair for the duration of an action film, every night, for like, the rest of his life.

He tried to wrestle his comedian-in-training glasses back on to watch the rest of Dean’s set, succeeding for a while, until Dean sang the end of the Mary Tyler Moore Show theme song (Cas had no idea it was The Mary Tyler Moore Show theme song). Goddamn the man’s singing voice. Cas stared, glad that he knew for a fact that the stage lights rendered him invisible to the performer.  

…………………………………………………………………………

“So how long have you wanted to screw your buddy, Dean?” Meg Masters plunked herself down next to Cas at the bar, sliding him some hipster beer, which was usually an indication of her interest in sex.  Cas glanced around the Laugh Shack to get tabs on Sam and Dean’s locations before turning back to the bar with a grim expression.

“I can't remember when it started. In the beginning I incorrectly believed I wanted to emulate him. I suppose that's still true, to a degree.” He let his eyes droop. Meg watched him as she took a swig of her drink, then swung herself around to examine Dean, standing in the middle of a group of newcomers who seemed to be complimenting his set.

“He's something, alright.” She managed to meld sarcastic and wistful, all with a silky murmur. Castiel suddenly wanted to touch her hair. “You think we could trick him into a threesome?” Her eyes flashed wicked, and her hair suddenly seemed much less enticing. Cas must have given her his most serious glare, because she immediately held her hands up in surrender. “Joking! Christ.” She stood up from her stool and put a few singles on the counter.  “I’m gonna go see if I can find anyone hot who doesn’t make me want to poke my eyes out when they open their mouth.  If I fail, which I most assuredly will, can I crash your place?”  She pasted a sickly sweet smile on her lips and danced her fingers up Castiel’s sleeve until she reached his shoulder, then diving in to tickle his neck.  He shrugged into it with a grin and gave her a nod.  His libido wasn’t so demanding tonight that he couldn’t leave all his eggs in Meg’s longshot of a basket.

“Goodnight, and good luck.”  He toasted his almost empty beer.

“Psshh.  More like ‘see you later’.”  She rolled her eyes.  “And don’t have too many more of those.”  She took his now empty bottle and plunked it on the counter.  It was Castiel’s turn to roll his eyes.  He gave Meg a small smile as she walked away, then let his eyes go soft until he focused in on his roommate Sam, standing at the bar next to a pretty woman with serious eyes and a pixie cut.


	6. Chapter 6

**Summary for the Chapter:**

> Everyone in the octagon house waives their right to remain silent.

“Cas, this is Donna.  Have you met Donna?”  Dean whipped around on his bar stool to smile his most proudly drunk grin.  Cas smiled at the blonde woman sitting next to Dean, who waggled her fingers at him, shyly.  Cas was immediately struck by her pretty face, framed with long shiny blonde hair.  He could tell Dean was admiring it too as he let his stool slowly drift around until she was back in his eyeline.  He licked his bottom lip.

“I haven’t met Donna.  Hello, Donna.   Now, if you’ll excuse me, I think I left our oven on.”  Cas pointed towards the exit as if that would be all the explanation he needed to provide.

“Dude.  Sit!  Chill.  You pay the bills.  It’s not like the house is gonna explode.”  Dean patted the barstool next to him, and Donna gave Cas a welcoming little nod.  

“Dean tells me you’re all comedians living in an ‘oct-a-go-nal’ house.  Sounds like a crazy movie plot.  Your life must be a hoot.”  Her Minnesotan accent was thick and endearing, even if it did somehow make her seem older, or slightly out-of-place in their scene.

“What does it mean to be a ‘hoot’?”  Cas asked, quizzically.

“Short for hootenanny?”  Donna looked worried that Cas was taking the piss, but kept her smile bright.

“A laugh riot.” Dean explained, reassuring Donna of Cas’s legitimate cluelessness.

“More fun than a barrel of monkeys.”  Donna added, eyes twinkling at Dean as if this were a back-and-forth that had easily bloomed between them.

“Non-stop chuckles.”  Dean’s attention had honed back in on Donna’s pert lips, which left Cas free to make his intended escape.

“Yes. I concur. However, in all honesty, Sam is behaving very suggestively towards that woman with the short hair, and I had overheard something about her being in law enforcement.”  He gave Dean’s back a stern look, in an attempt to communicate that the communal bong and all its accouterments were currently strewn over the coffee table in direct eyeline of the front door.

“Yeah yeah yeah.  So is Donna.”  Dean answered without breaking eye contact with the perpetually blushing woman.  “They’re at a sheriff convention.  They’re sheriffs.  She’s got a gun.”  Dean pried his eyes away to smile goofily at Cas.  Donna tried to internalize her fluster, and gave a little eye rolling sigh to acknowledge that she was indeed awesome for being a sheriff.

“Oh. Well, while I am in awe of your vocation, I think it would be good to tidy up the house a little in the event that Sam… decides to entertain.”  Finally, Cas’s message penetrated Dean’s haze, and his friend turned to give him a nod and a thumbs up.  But as Cas lifted his hand to give a final wave, he was rudely interrupted by the booming voice of a drunken fool.

“Hey Donna! Getting the guy drunk is gonna backfire, bigtime. Then he'll just see two of you!” The most obnoxiously dorky, overaged dude-bro laughed raucously at what he appeared to believe was a joke. 

“Oh Jebediah in a jelly jar.” Donna muttered, twisting away from the sound and reaching out to clutch her drink with two hands. 

“Who's that?” Dean asked, squinting. 

“That's Doug, my ex.”  Donna kept her eyes cast down, in shame.  Cas frowned at her shrinking countenance, and opened his mouth to question further, but was cut off by the Doug character. 

“You talking to both those guys, sweetie? At this point I guess there's enough of you to go around!” Doug had an audience of one other totally blasted male sheriff, who was making exaggerated ‘oh shit’ faces at every remark. 

“What the fuuuuck?” Dean's voice trailed off at the end in utter disbelief, and his hand moved to Donna’s knee to give it a little squeeze.  Cas smirked when he caught the Winchester’s digits wandering in the corner of his eye.

“How long did you date? He doesn't seem to have many visible attractive qualities.” Cas turned his head slowly, and stared Doug down with laser intensity. 

“Married. He’s my ex husband.” She took a long sip of her cocktail.

“You  _ married _ that guy?” Dean jerked his thumb over his shoulder and asked a little too loudly. 

“He was a lot nicer when I was thinner.” Her shoulders slumped and she began to kick her foot into the bar like a pouty child in church. 

“I don't know what that means.” Castiel spoke like a suspicious robot. 

“It means I'm about to put a total douchebag in his place.” Dean stated, starting to rise out of his chair and push up his sleeve like any pure-hearted man who’d blow  a .15% BAC if questioned. 

“No.” Cas grabbed Dean's bicep and pulled him back down. “I think I would rather proposition him instead.  I’ll see you at home.” Cas released Dean's arm and breezed across the room, coming up too close to Doug too quickly. 

“Am I to understand you are dateless this evening?”  Cas held his tan trench coat over his arm and stood stiffly in front of the astoundingly asinine Doug.

“Who's askin?” Doug glanced at the bar and tried to wink at a Lisa as she laughed loudly at her friend Jo over by the hostess stand. 

“I am asking. I'm interested in dominating you in a sexual manner.  My name is Castiel.” He offered his hand.  Doug did not shake it. 

“Wha? Look, guy, I'm straight. All the way. 100%.”  Doug held his hands up as if to surrender, failing to keep the disgust from bleeding into his voice.

That's statistically unlikely.  You are clearly trying to make yourself repellent to any and all females by publicly degrading one of your past love interests based on her weight. Luckily, I am a very fit man. I believe the activity I am suggesting would be referred to in the vernacular as a ‘hate fuck’.”

“Lookee here, buster.”  Doug tried to muster all the physical presence of a yelling person, but spoke only in a strong whisper.  “Yer sexually harassing an officer of the law in front of multiple witnesses.”  Doug’s hands twitched up to uneasily rest over his kidneys, bowing his elbows out behind him like chicken wings.  It was a puzzling choice of stance.

“Why are you whispering?  You had no problem telegraphing your lack of sexual attraction to your ex-wife across the whole establishment.”  Cas held Doug’s gaze while taking a page out of Dean’s book, and letting his fingers float over to Doug’s side and trail lightly over Doug’s hand.

“What the-!”  Doug pulled his hand away like he had been burned, and rubbed the tickled skin of the back of his hand onto his khaki-clad thigh. “You're lucky I'm out of my jurisdiction, or me and my deputy would have your ass so fast!” Doug’s eyes flicked around to locate his backup, but the man had gotten drawn into watching a game of darts, and was no longer there to offer his patented “oh shit” perma-whoa.

“Is your deputy attractive? Where exactly is your jurisdiction?” Cas gave Doug a calculating up and down. The asshole made it all too easy.  “We can be democratic about whose ass will be had, and draw straws.”

Donna and Dean had both been trying very hard to appear as if they were ignoring the exchange, but Donna snorted into her hand at the last remark.  Cas resisted turning around, but his lip attempted to twitch into a smile before he schooled his face back into the bitter scowl of a defied headmaster.

“If you’re sure about refusing my advances- “  It was Doug’s turn to snort, but Cas continued “ -then I suggest you leave before you are forced to watch your ex-wife go home with the most beautiful man you will ever encounter in person.”  

Doug’s body reacted as if Cas were threatening him with physical violence before the sentence fully processed, at which point the man deflated like a worn out whoopie cushion, coughed awkwardly into his fist, then backed away, unwilling to turn his back to Castiel for the first couple of feet.   Cas gave the empty space left behind a mental eye-roll, then swirled his trench coat out of his arms, hands deftly diving through the sleeves and primping the collar as he finally managed his own exit.  It was a night of missions, and Cas had now tasked himself with legalizing their home before any of his roommates returned with officers of the law.

“Aw.”  Dean leaned an elbow on the bar and rested his chin on his hand.  “Cas thinks I’m pretty.”  He smiled, his happy-drunk high settling back over him like a warm blanket.  Donna scoffed.

“He’s not the only one, don’tcha know it.”  She winced slightly at the slip of such a stereotypical colloquialism, then brought her drink up to sip through the tiny straw.  Dean followed with his eyes.

“I think you’re pretty, too.”  This was a line that wreaked of high school, and first times, and fumbled confessions in the closet during seven minutes in heaven.  Dean was aware.  He was also aware of the way Donna had been drinking only diet rum and cokes, had checked behind herself several times to make sure he was actually talking to her, and had once made vows to spend the rest of her life with a total asshat.   Dean circled his thumb where it had been wresting, just above her knee.  Mostly-innocent was his plan, and yes- he had a plan- because Donna’s smile was 1000 watts and she kept biting her lip after letting her Minnesotan slip out and between her shampoo and her perfume she smelled like strawberry cupcakes and Dean’s subconscious kept barging in every five minutes with delightful suggestions of all the adorable exclamations she’d yell out in the throws of passion.  Jesus Christ, that clown probably didn’t know the first thing about decent sex, and she fucking married him because she thought he was  _ nice _ .  Dean on the other hand could probably successfully pleasure an irate, snake-haired Gorgon, if his life depended on it.  And he was nice to boot.  “And pretty people like us, we gotta stick together.”  He pulled himself up with a sobering breath.  “It’s a mess out there.”  

“Oh, for sure.”  Donna nodded, playfully patronizing.

“Right?”  Dean smiled.  “You’ll just have to protect me, while you’re here.”  He held Donna’s gaze, but zoned out a little thinking about how freaking hot she’d be at a gun range, all business and deadly, paired with that cherry cheeked smile.

“Please, for all that is holy, do not say you’ll be his ‘police escort’.”  A new female voice cut in as the woman with the dark hair and a pixie cut leaned on the bar next to Donna to look in on their conversation.  Donna straightened up with a small pout.

“Hi.  I’m Jody.”  The woman smiled at Dean and offered her hand, which he reached awkwardly over the bar to shake, his eyes wandering to find Sam standing behind Jody, wearing an unreadable expression.  “Donna is my roommate for the weekend.”  Donna gave Jody a smile, then let her shoulders slump like a teenager who was about to get in trouble.  Dean let go of Jody’s hand, suddenly threatened by the very sober looking roommate.  “I’ve just been talking to Sam here, and he seems to think he can handle a more experienced woman.”  She reached back and squeezed San’s bicep in an exhibitory fashion.  Sam blushed.  Dean unleashed a slow grin as he wondered what exactly his little brother had gotten himself into.  Donna cocked her head to the side and tried to stifle a smirk.  “Word is, your house is an octagon.”  Jody let that statement sit for a moment, blinking a couple times to demonstrate her dry wit.  “Sam was just going to show it to me, but since we’re both sober we thought we’d better ask if you two need a ride anywhere.”  Donna gave Dean a coy deer-in-the-headlights, her confidence constantly bottoming out at each interruption.  Dean tipped his head forward and gave her puppy dog eyes through his lashes.

“Eight exterior walls.  You know you wanna.”  His voice was a low, gentle smolder.  

“Oh- okidoki.”  Donna choked out.  

Dean stood up and reached for his wallet, paying their tab and leaving a generous tip.  Sam wandered over, buzzing with nerves and anticipation, like a neon sign.  Dean dug back into his pocket and produced the keys to the Impala.

“You’re driving?”  

Sam nodded.

“I’ll follow behind you guys with our rental.  Keep me company?”  Jody asked Donna.  Donna nodded as she slipped into a thin, black leather jacket, reaching along her neck to flick her hair out from under the coat.

“Great.  Guess it’s time for you to meet the Impala.”  Sam joked.  Dean bumped his brother with his elbow and headed towards the door, with Sam sauntering behind.

“Lands alive, I thought you were gonna make me go back to the hotel.” Donna released the thought at Jody in a rushing escape of air. 

“Psh.”  Jody plucked Donna’s bag from the back of Donna’s stool and handed it to her.  “You told me not to let you do anything stupid.”  Donna looked suddenly crestfallen, so Jody continued.  “Missing out on a night with a stunning guy that's spent the last hour looking absolutely smitten with you?  Now that would be stupid.”  Jody shooed her friend towards the door with the grin of a very maternal madame.  Donna giggled.  Somehow, with his super-sonic cuteness radar, Dean heard said giggle, and stopped to turn and give her a wink and a head jerk towards the door, in an attempt to hurry them to their vehicles.

………………………………………………………………………………

Castiel’s legalizing spree turned into a cleaning spree as wiping up resin continued on to coffee splatters and the light sheen of oil on the stovetop.  It was the power of Sam’s as-seen-on-TV micro-fiber cleaning cloths. Cas was known to get carried away.  

He twitched when he heard the front door, then whipped the cloth back towards the sink, and walked to the kitchen doorway to greet his roommates, rubbing his damp hands together for lack of anything more inspired to do with them.

Sam and Jody entered first, Jody holding Sam’s hand very matter-of-factly, as if they were simply trying not to lose each other at a crowded zoo.  Jody spotted the sitting area, and led them to it, before releasing Sam, who immediately moved to put on some music to play in the background.  Dean helped Donna off with her jacket.  This ended with him letting his fingers play through her long hair, and leaning in close to mumble about how much he admired it.  That was apparently the straw that broke the back of Donna’s camel of shyness, for she managed to close the distance and finally get her mouth on Dean’s, all while his hands were still tangled in her hair.

“Oh good.”  Jody had been craning her head to watch, and she uncrossed her legs and stood up from the couch.  “No need to awkwardly chat.  Let’s grab a drink, and then you can show me your room.”  She leaned her body close to Sam’s for a moment, and flicked her eyes up to his, before picking a piece of lint off of his chest, and backing slowly towards the kitchen.  Cas slipped out of the doorway to make room for the sauntering woman.  He raised his eyebrows at Sam, who returned the look with a micro-shrug and a smile.

Dean and Donna hadn’t managed to pause their kiss, and Cas was relieved that Dean’s bedroom was closest to the entryway.  Even so, it didn’t look like they were going to make it there any time soon.

“How drunk is she?”  Cas asked the air, assuming Jody was still in earshot and not currently swallowing Sam’s face.

Earshot, yes.  Not swallowing Sam’s face?  No.  She had actually pushed herself up to sit on the counter so that she could straddle the standing Sam to get closer to his mouth.  She let go of the younger man’s bottom lip with a loud smack, and a sigh.

“Sober enough to consent, and drunk enough to not let her low self-esteem ruin a good time.  Lord knows she deserves it.”  She began to unbutton Sam’s shirt.  Cas was still watching the lovers near the front door.  Sam was starting to breath more audibly.

“Hmm. Yes.  Doug.”  Cas was in agreement that Donna deserved a good time.

“C’mon big boy.  Let’s go count your walls.”  Jody gave a little hop that Sam correctly read as an invitation to pick her up, grasping her strong ass, all smiles as he walked her to his room, and kicked the door shut behind them.

Cas turned to look when he heard the door slam.  Another slam from the opposite direction followed immediately after, and he turned back to find he was suddenly alone in the living room with nothing but Sam’s soft mood music left playing for no one.  Cas walked over to the couch, and sat down with a pout.  As tempting as it would be to go to his room and touch himself to the snippets of sex noise he might be able to hear from Dean and Donna, it didn’t seem prudent.   He would simply have to wait on the couch for a while, keeping his dick safely in his pants, and fervently hoping that Meg would show up and help him displace all the sexual energy he’d seemingly collected from breathing the air in the room.

…………………………………………………………………………….

Sam Winchester, despite his soft soulful eyes, fully prescribed to the tao of the one night stand.  Sheriff Jody Mills seemed to be on the same page, but where other girls sometimes laid themselves out, almost hysterically writhing and moaning to illustrate their untamable desires, Jody proceeded with all the measured grace and patience of a woman who knew she would only be doing this once.  Her moans sounded like they were a surprise to her, and her expression told of a person who had shit to do.

Sam basked in the attention for a while, his mind still jumbled with the rush of seduction.  She had him shirtless on the bed as soon as the room door slammed, tossing his flannel and tee shirt aside to create a hint of chaos in his otherwise orderly room.   Soon after, she unbuttoned her way through his button-fly jeans, huffing a laugh for no explained reason.  Either way, it served to make Sam a tad self conscious.  He switched the focus to undressing Jody, stopping for a nano-second as he ran his hands up her torso, and noticed the ghosts of a hundred stretch marks clustered around her belly button.  He didn’t dare meet her eyes as she moved her hand to cover her belly.  She kept that hand moving down, brushing lightly over her black satin panties then doing the same over Sam’s boxer briefs.  

At this point, Sam realized  that they had reached their current destination with a minimal amount of kissing.  This could possibly be attributed to Jody’s all-business style of flirting, or the fact that they were two designated drivers quickly approaching the time of night when all good sober people’s bodies give up on consciousness. Whatever the excuse, he endeavored to remedy their mistake, timidly sitting up to peck at the side of Jody’s mouth.  Her hand stilled on his hardness as she smiled involuntarily, then turned her head slightly to capture his lips in her own tentative kiss.  She sucked on his top lip, pecked at his lower lip, then ran her tongue quickly under the bow before pressing forward again, her lips parted slightly, simply to let him feel as she sucked in a stuttering breath, cooling and tickling his kiss-moistened mouth.  It was Sam’s turn to grin.   _ Wow. People forget how physical the response can be from stimulating erogenous zones other than the nipples and genitalia,  _ he marveled as he snaked a firm hand around Jody’s waist, to press on the small of her back.  She threw her arms around his neck in response, and they proceeded to play tonsil hockey until the friction between their groins became too good to ignore.

………………………………………………………………………………..

Castiel was eyeing the living room like a person who’d just unexpectedly been granted some time home alone.  He took his time considering his options, before rolling the royal blue exercise ball out from under Sam’s small laptop desk, and lowering his bottom down gingerly.  It was bouncy.  He was pleased.  He pulled up the music program and went searching for a station that that better suited his mostly content, but rather sexually frustrated mood. 

……………………………………………………………………………….

Meanwhile, Dean had not been too inebriated to pull out all the stops for his blushing house-guest.  Instead of switching on the harsh, overhead light fixture, he fumbled around the dark until he managed to plug in the string of white LED lights that he’d hung artfully above his bed.  They were set to twinkle, softly.  Donna rolled her eyes, before letting them roam around the room, curiously.  She asked about a few of his trinkets, and he answered, giving short but emotional anecdotes about whatever she pointed to.  He unbuttoned his overshirt and tossed it over his desk chair.  Donna wore her best perma-smile as her eyes seemed to search for another way to waylay the progress that had seemed so effortless in the glaring light of the hallway. 

“Did you fly here, or drive?  For the conference.”  Dean asked her, face purged of all smoulder, his eyes open and kind.

“Oh I flew. Had a lot of miles saved up, and nary a vacation plan in site.”  She joked, obviously more at ease when chatting.

“Shit.  Well I know exactly what you need.”  He waked over to the bottom drawer of his desk, and pulled out a narrow bottle of oil.  “A massage.”  He held it up with a grin.  “How about it?”

Donna took a steadying breath, and looked around the room for an answer. Dean bit his lip, wondering if he'd just blown it. He already knew from experience that pointing to the parts of a full-figured woman’s body that she considered most unforgivable, and declaring that he was more than cool with them, and wanted to get his mouth on them would end in physical violence towards his person, or at the very least, strong suspicion that he was some sort of fetishist.  He thought the massage was a stroke of brilliance- a way to demonstrate his admiration of her body without jamming his foot in his mouth. 

“Are you any good?” Donna asked, chasing away his worries with a comical quirk of her eyebrows. “Because I have what's known around my parts as 'magic fingers’.” She held up her hands and waggled her digits.

“Then by all means, you first.  I’m always tense after a show.  But don’t think you’re getting out of it.” Dean winked, stripped off his tee shirt, and flopped into the bed. “I'll just be here taking notes.” He rested his head on his folded arms, and closed his eyes, with a shit-eating-grin left lingering to effectively ruin the picture of innocence.

“Hoo boy.”  Donna slid her flowy pink sweater off of her shoulders, leaving her clad in a strappy white tank top and some painted-on jeans. 

“Any day now, Dimples.”  Dean groused as he fake yawned.  “Oh wait.”  He hopped up from the bed and stripped off his jeans.  Donna looked perplexed, but not flustered.  That was a good sign.  “I like to give my masseuse full access to the glutes.”  He explained.

“Way to make a girl feel special.”  Donna deadpanned as her hands reached for the fly of her own jeans.  Dean borrowed a move from Cas and hit her with a quizzical head tilt.  “I need freedom of movement when I’m straddling my clients.”  With that she shimmied out of her jeans, giving them a fun little kick as the last leg reached her toe.  Her legs were pale, but shapely, nicely toned from years of walking a beat, complemented by an ass that had clearly seen its share of squats.  Her panties were pink satin. Dean didn’t look away.  “Alright, mister.  On your stomach.”   She put her hands on her hips, and Dean’s tried to tame the raking of his eyes down to match the soft  twinkling of the lights.  He pouted for a moment, before his eyes lit up once more.  He turned and reached into his closet, emerging with a full-length dorm mirror which he slid into the space between his bed and the wall.  He then settled himself back down on the bed, this time with his arms wrapped around a pillow, effectively propping up his head so that he could watch anything occurring behind him.  Donna ignored the mirror as if it were a pesky, low-angled camera, flicked her hair over her shoulder, and climbed over him with a muscled control that made him internally groan with anticipation.

“Now, the secret to a good massage-” she started in a partially distracted voice as she looked over the label of the massage oil- “is mixing a little bit of pain with your pleasure.”  She poured a handful of oil, and slicked it between her hands, then, standing high on knees, which were on either side of Dean’s thighs, she slid her palms slowly up Dean’s back.  

Dean enjoyed the view as her biceps nudged her breasts together when her hands reached his shoulder blades, but he couldn’t keep his eyes from rolling back when she raked her nails lightly back down the same path.

………………………………………………………………………

“But you couldn’t have arrested him for that?”  Sam was sated and relaxed, head propped up by one elbow at the foot end of the bed. 

“Little did he know.”  Jody answered, wryly.  She had slid back into her panties and adopted Sam’s tee shirt.  She laid in the bed on her back, hugging an old pilly pillow.  “How do you know?  You got a record?”  She raised an eyebrow at her bed-mate.

“No.  Just some degenerate friends.  And half a law degree.”  He muttered the last sentence, then reached over and began to flick Jody’s toes, playfully, in a transparent effort to avoid the lecture that was surely oncoming.

“Lawyers can be really awful people.”  Jody told the ceiling.  Sam looked up from his foot flicking, surprised.  She didn’t make eye contact, continuing to pick and flick balled up bits of cotton from the case on Sam’s favorite headrest.  Perhaps he had mentally assigned Jody a little more of a motherly persona than she would appreciate.  

“Yeah.  Well, you know.  We comedians are the salt of the earth.  It’s a very selfless path, I’ve chosen.”  Self deprecation wasn’t something Sam often tried out-loud, but he was reclining in the comfort of his own room.  He felt safe.

“There’s something about you two- or you three, I suppose.”  Jody inched her head up, trying to find a way to prop it in Sam’s direction.  “I mean, I only got to see Dean tonight, but I can tell.  I’ll bet you boys are gonna make it.”

“Make what, exactly?”  Sam snarked.  In the dark of his more debaucherous evenings, it was easy to believe that the octagon house was going to be the pinnacle of his earthly experiences.

“Whatever you want.”  Jody smirked, and her smile told of all the concessions she had made in order to allow herself to go home and spend one night with a man at least 15 years her junior.  Sam blushed.  It wasn’t a reaction to embarrassment as much as a physical side-effect of the battle between his need to fuel his persona of manliness and a gnawing urge to show Jody his college transcripts.  Okay.  At this point it would be safe to say that Sam had some mommy issues.  Time to cough out a laugh, clear his throat, and file those away somewhere that they could be useful for future comedy.

“I, uh, wrote a pilot for a sit-com, if you wanna read it.”  Sam bit his top lip, and not in the sexy way.  Jody just smiled, and clamped down on excuses about her not being in show business, and the sheer uselessness of her opinion to an accomplished entertainer like Sam.

“I’d like that.”

………………………………………………………………………….

_ I don’t know how I ever thought this woman was shy _ Dean thought, gleeful about his incorrect assumption as Donna raked her nails over his scalp, pushing his head between her legs even harder, and arching her back with a gasp.

“Jesus H. Jon Benjamin!”  She cried in ecstasy.  Dean giggled directly into her ladybits, which only elicited more nonsensical exclamations.  “Ohhh, chris cross ya don’t stop.”  

Unfortunately for Donna, that last statement left her lover doubled over with laughter.  She let a wave of heat pass over her- presumably shame or regret or one of those other emotions that fucked with her self image.  Luckily, it coupled nicely with the bliss of some amazing oral sex/ manual stimulation.  She was panting.  She concentrated on catching her breath.  She’d already come too far for this to end poorly.  She could see the home stretch of a race she was surely going to win.

“We should have recorded this.”  Dean murmured against her skin as he slid his mouth up her body, propping himself up on strong arms as he climbed up the bed.  “You,” he kissed her neck. “Have,” he pecked under her jaw. “The most,” he kissed her cheek, oddly tender. “Amazing,” he licked her earlobe, then leaned in to finish his thought. “Reactions in the history of sex. Ever.”  He propped his head up on his elbow, but let his free hand wander back down to naughty territory.  Donna squealed.

“I’m sorry,”  Donna panted, miraculously struck with lightning-fast repartee.  “But where I come from, ‘sex’ involves a little less chit chat and a little more riding you into the sunset.”  She was up on her knees, peeling off Dean’s boxers before he could register the manhandling.  Regardless, he consented.

“Well giddy-up, then, princess.”  He stuttered, as she produced and applied a condom as if it were a Spiderman-like secretion coming from the palm of her hand.  The lights above his head seemed to twinkle faster.  Everything felt sticky in the best way, and the sensations coming from his manhood left nothing to be desired.  Without thinking he folded his hands behind his head.  Donna cracked an eye open to take in the scene, and snorted.

“You dick.”  She laughed.  Dean gave her an evil grin, and bucked his hips up, causing her to ‘oof’ as she jutted into the air.  “Holy Moses in the river.”  She exclaimed, before setting her jaw and narrowing him with a glare that he didn’t fully feel the heat of until she was pinching both his nipples with a vengeance.

“Oh hell yes!”  He gasped.  The little comedian in the very back of his mind took a moment to lament his complete lack of creativity in the presence of such an exclamatory genius.

……………………………………………………………………………

The noise from Sam’s side of the house having quieted down, Cas found himself in the kitchen, mixing up some gluten-free brownies from a mix that Charlie had accidentally purchased while shopping with the munchies, then subsequently dumped on them in disgust.  But brownies were brownies, and chocolate paired nicely with the earl grey he found in the back of the coffee cabinet.

The living room Pandora station continued to play, now too quietly for him to hear over the noises of his kitchen muddling.  He searched around and located the stereo remote control, and pumped up the volume a few clicks.  The channel seemed to have strayed from his original vibe, which had been some popular indie song by a so-called Band of Horses, but Cas wasn’t bothered.

……………………………………………………………………………..

“Um.  I’m not sure what’s going on out there, but.”  Sam had been sitting at his desk watching Jody read his script, and making a conscious effort not to wring his hands, when suddenly there was a melodic raquet coming from the living room. 

“It sounds like someone married a non-violent protest with a really awful pop song.”  Jody quipped, possibly feeling creatively inspired by her easy comprehension of the many symbolic layers of Sam’s screenplay.

“Yeah.”  He turned his head towards the door.  The sound didn’t stop.  “I’m just going to go…”  He reluctantly stood up.  Jody waved the hand holding the read portion of Sam’s script, without looking up.  Sam took it as permission to leave.

…………………………………………………………………………..

“Jesus. Why is hell Pink rapping in my house?”  Dean was brought out of the after-glow of his pleasure by the dulcet tones of a bleach-blonde pop-star. 

“That damn Kesha made it look too easy, don’tcha know it.”  Donna groaned, though she breathed a little easier when Dean pulled his arm off of her chest.  It was a weight she was mentally sad to be rid of.  “It’s sad.  There’s no one in her life that loves her enough to tell her how god-awful this is.”  Donna seemed to experience an after-glow of emotions.

Pink continued to ‘run it’ like she’d been there and done it.

“Alright.  I gotta shut this down.”  Dean groaned.  He stepped into some boxers, and made his way to the door, giving Donna a wink before his exit.  She rolled over and hoped to god she wasn’t snoring when he returned.

……………………………………………………………………………

The three roommates convened in front of the stereo.  Dean and Sam each in boxers, no longer moist or musty, but still a commanding testosteronal presence in the otherwise neutral living room.  Cas felt overdressed and underused, and the only evidence of his deviance was the chocolate spatters on his shirt front.

“What the hell is this?”  Dean demanded with a vehemence that anyone except Sam and Cas  would immediately interpret as genuine anger.

“This is the artist Pink, Just Like Fire.”  Cas answered, mechanically, as he scanned the room for the stereo remote.

“Why is it happening?”  Dean asked, this time genuinely curious.

“It’s Pandora’s fault.  This song is recorded louder than all the others.  I did not choose this.”  Cas defended himself.  Sam stood with his hands on his hips, amused, still sober, and very tired.

“This is your fault.”  Dean jabbed a finger at his brother.  Sam didn’t bother to argue the absurdity of the accusal.

“ _ No one can be just like me, anyway. _ ” Sam sang to Dean with shocking accuracy of timing and pitch, even though it was well outside his natural range.

“What, did she castrate you?”  Dean jibbed.

“I apologize for interrupting both your evenings, but I can’t find the damned remote.”  Cas piped up, exasperated at the parley that seemed to be entirely the fault of his bad luck and negligence.  Sam sniffed the air with a thoughtful head tilt, then wandered towards the kitchen.  Dean huffed and rolled his eyes, then reached out all of two feet and turned the stereo knob manually.  Cas looked up with an eyes narrowed glare that seemed to blame Dean for his non-technical upbringing.  Sam wandered back into the room, shaking the remote that he’d found in the kitchen in front of himself.  He placed it on its designated side table with a pointed look at Castiel.  

“Right,”  was as much of an apology as Cas could muster.  It wasn’t for his good time that all of their illegal narcotics were on lockdown.  The man was having to make do with the polyphenols of organic cocoa.  They were going to have to cut him some slack.

“Yoo hooo.  Casper the friendly Clarence.”  A voice wafted from the entryway.

“That would be Meg.”  Cas stated, returning to the original circle of confusion that they had formed around the stereo.  Sam raised his eyebrows, but continued to look very chill.  Dean scowled a little.  The octagon house didn’t do a lot of repeat business, and if it were going to start, he certainly wouldn’t choose Meg as the woman who’d change it all.   

“Yay!  Hot man party!  Which one of you lumberjacks is gonna help me climb Cas this evening? Paper, rock, scissors that shit, ‘cause thought of Wincest- “ she gave an uncharacteristic shudder- “that shit turns me off.”  She ended, in a silly voice.  As if the Serpent had entered their garden, Sam and Dean were suddenly made aware of their nakedness.  Cas sensed the change in atmosphere, and took one last whiff of the air between him and his friend/ secret physical crush, trying to find some Dean under the almost cloying cloud of chocolate.  

Dean didn’t notice, as he was trying to discern a walking route back to his bedroom that didn’t involve giving Meg an up close and personal show.  Granted, if she hadn’t asked for it, it would have been on his terms, and he likely would have been all for it.  However, with the threat of a threesome with another dude hanging over his head, those waters seemed too perilous to fish for an ego boost.  Anyway, the now-patented Donna-isms had been enough, at least for that night.  He couldn’t deny that he would soon need more.  Such was the life of the broken comedic performer.

“Break on three.”  Cas held his hand out to the middle of their circle.  Sam swallowed his laugh and complied, while Dean added his own with all seriousness.  Cas had come to live with them under the auspices of comedy advice, but Dean had quickly realized that his roommate was trying desperately to recapture something he’d missed out on in his time as an abandoned child of God.  Whenever Cas put a scene from a popular movie into motion, he wasn’t attempting to fit in, he was testing the theory of whether he would ever catch up, and trusting his roommates to backtrack a little, for his sake, and accept him in the event that he never could.

“What do we say on break?”  Sam asked.  Cas and Dean stared at him until he was forced to decide for them all.  “Alright.  Uh, ‘octagon house,’ on three.” 

“One. Two. Three. Octagon House.”  They chanted, raising their hands on the break.  

“Ass, ass and pussy.”  Dean echoed himself, hand in slow motion in the air after the break.  “Sex with strangerssss.”  He mimicked the voice of a man falling into a deep chasm.

“Is he stalling for a real invitation?”  Meg’s voice came from directly behind them now.  Dean jumped.  Sam just shook his head and walked back to his bedroom, disappearing as easily as a moose among pines.  “Because I don’t have it in me.”  Meg confessed.  Cas smirked at his friend, and led her back to his room, secretly relieved that Meg’s level of enthusiasm probably wouldn’t make it through his shared wall.

…………………………………………………………………………….

The next morning, all members of law enforcement were up and at ‘em with the sun, due at a gun control seminar by nine.  Goodbyes were offered in the privacy of their host's bedrooms, though the two women had trouble containing their giggles as they picked their way out of the house, trading accusing glares that jokingly screamed  _ you little harlot! _

Donna had told Dean to look her up if he were ever near Hibbing.  She’d faltered a little at the end, adding that he could bring Sam or a girlfriend or whatever because she understood it was just a one night thing.  Dean saved her from her bumbling by admitting that he’d genuinely like that, and putting her phone number directly into his cell, then texting her so she’d have his.  Once again, he struggled to find the words to assure her that she was a cute, sexy, and delightfully funny woman who any man would be lucky to catch.  Because telling her would imply that it needed to be said, and he didn’t really feel that it was appropriate to acknowledge that there were people in the world who might feel otherwise.  He’d text her later.  He’d beg her to add her Minesota-isms to her text-speak, if he had to.  He was feeling more entitled to pockets of innocent happiness, in his older age.

Jody had fallen asleep with Sam’s pilot script on her chest, and awoke from dreaming of the witty banter of three monster-hunters that Sam had invented.

“What are you laughing at?”  He’d asked, feeling more awkward as they conversed face to face instead of face to feet the way they relaxed the night before.

“Your script.  It’s great.  I had a dream about it.”

“Really?”  Sam’s inner child burst forth, and nearly brought a tear to Jody’s eye.  “I don’t know.  I thought it might be missing something.”

“Well.”  Jody started, slowly.  Sam braced for criticism, the way a skunk-sprayed dog braced for a tomato bath.  “It is.”  Sam blinked, then sighed.  Jody was astute, she could tell something was missing, but she wasn’t a writer.  She was a cop.  She wasn’t going to come along and fix his writing.  It was never that easy.  “What it’s missing,”  she continued, ignoring Sam’s deflation, “is a kick-ass sheriff.  You know, one of those cougar types.”  Sam laughed, and Jody giggled for the first time since they’d met.  She was joking, poking fun at herself, but Sam realized she was right.  He’d borrowed the main characters from his life.  They were Dean and Cas and Ash and Garth and Charlie, but there was no one like Jody.  There never had been, and there likely never would be again.

“I think you’re right.”  He mused.  Jody hit him in the face with a pillow, then ordered him to go back to sleep.

Dean finally pulled himself out of bed at eleven, and found Cas in the kitchen, eating brownies straight from the pan, with a full glass of milk at his side.  He offered Dean a fork, which he accepted.  

"How was your night?"  Dean asked around a hunk of gluten-free chocolate goo.

"Average. Meg gave me a halfhearted blow job, mounted me, came, and then passed out. I manually stimulated myself onto her suede shoes, and she was none to happy when she regained consciousness."

Cas stared at Dean as Dean choked on a brownie.  He had gained Dean’s friendship, almost instantly, and possibly eternally, but he was going to have a hard time stopping himself from stealing moments of something that to him amounted to more than platonic companionship.  He’d at least perfected his stoicism as he cataloged these events directly into his long-term memory.

“That’s uh.”  Dean achieved his normal breathing pattern.  “That doesn’t exactly sound like the way to keep ‘em coming back.”  He counseled, carefully.  Cas tilted his head.

“Probably not.”  Cas conceded, then scooped another gob of undercooked cake into his mouth.

Dean searched for any sign of regret on Cas’s part, but there was none, which somehow let him breath a little bit easier.

**Notes for the Chapter:**

> Firstly, please don't be offended at Dean's reaction to that Pink song. That is not me trying to secretly bash Pink. It IS me trying to subversively promote Kesha. So there's your full disclosure.
> 
> This took a long time to write. I literally had to abandon my family at 8 in the morning and drive to a coffee shop (because all the libraries are closed on Sunday BOOOO) so I am going to beta it later. I believe that I have been staring at the bulk of it for so long that there shouldn't be THAT much wrong... That's my belief. But I apologize.
> 
> I apologize because I really like this chapter a whole lot- in that way where I feel like someone else wrote it and I'm just a passive fan of it- so if that is ruined somehow by crappy typos, well that's just sad.
> 
> I'm going to have Just Like Fire in my head for the rest of the week/ month / year. Maybe you are too. You're welcome?
> 
> Also, sorry for the double-length chapter but it was all one piece. Yay for length. *wink*


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